GB1268867A – THE PREPARATION OF D-THREO-beta-p-METHYLSULPHONYLPHENYLSERINE ESTER
– Google Patents
GB1268867A – THE PREPARATION OF D-THREO-beta-p-METHYLSULPHONYLPHENYLSERINE ESTER
– Google Patents
THE PREPARATION OF D-THREO-beta-p-METHYLSULPHONYLPHENYLSERINE ESTER
Info
Publication number
GB1268867A
GB1268867A
GB4811171A
GB4811171A
GB1268867A
GB 1268867 A
GB1268867 A
GB 1268867A
GB 4811171 A
GB4811171 A
GB 4811171A
GB 4811171 A
GB4811171 A
GB 4811171A
GB 1268867 A
GB1268867 A
GB 1268867A
Authority
GB
United Kingdom
Prior art keywords
threo
ester
methylsulphonylphenylserine
give
optically inactive
Prior art date
1969-07-24
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB4811171A
Inventor
Hisao Akiyama
Hisao Tobiki
Toru Mitani
Yasuharu Miura
Hiroyuki Suzuki
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
1969-07-24
Filing date
1969-07-24
Publication date
1972-03-29
1969-07-24
Application filed by Sumitomo Chemical Co Ltd
filed
Critical
Sumitomo Chemical Co Ltd
1969-07-24
Priority claimed from GB37320/69A
external-priority
patent/GB1268865A/en
1972-03-29
Publication of GB1268867A
publication
Critical
patent/GB1268867A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
Classifications
A—HUMAN NECESSITIES
A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
A61K31/00—Medicinal preparations containing organic active ingredients
A61K31/16—Amides, e.g. hydroxamic acids
A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
A—HUMAN NECESSITIES
A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
A01N41/10—Sulfones; Sulfoxides
Abstract
1,268,867. Process for D-threo-beta-p-methylsulphonylphenylserine ester and the corresponding optically inactive free acid. SUMITOMO CHEMICAL CO. Ltd. 24 July, 1969, No. 48111/71. Divided out of 1,268,865. Heading C2C. Optically inactive threo-#-p-methylsulphonylphenylserine (I) is made by contacting optically active threo-#-p-methylsulphonylphenylserine ester with water and acid or base, adjusting the pH to 8 to 11 and heating the solution to 30‹ to 150‹ C. D – Threo – # – p – methylsulphonylphenylserine ester is made by the following steps: (a) 2 moles of p-methylsulphonylbenzaldehyde (II) are reacted with 1 mole of an alkali metal salt of glycine in alcoholic solvent in the presence of alkali metal carbonate, the mixture is acidified to precipitate unreacted II (remove by filtration) and the filtrate is neutralized to give threo rich I which is (b) esterified to give optically inactive threo-#-p-methylsulphonylphenylserine ester (III), (c) III is contacted with d-tartaric acid in a solvent to give crystals of D-form ester-d-tartaric acid salt (IV) which are separated from mother liquor containing L-form ester-d-tartaric acid salt (V); (IV) is contacted with alkali to give the D-form ester from the salt, and (d) the mother liquor from (c), containing V or an L-form threo-#-p-methylsulphonylphenylserine ester (obtained by adding base to the mother liquor), is contacted with water and base or acid to give an aqueous solution containing L-threo-#-p-methyl-sulphonylphenylserine, thereafter the pH is adjusted to 8 to 11, the solution heated to 30‹ to 150‹ C., cooled, the pH adjusted to 3 to 4 to precipitate optically inactive threo-#-p-methylsulphonylphenylserine which is recovered and recycled to the esterification step (b).
GB4811171A
1969-07-24
1969-07-24
THE PREPARATION OF D-THREO-beta-p-METHYLSULPHONYLPHENYLSERINE ESTER
Expired
GB1268867A
(en)
Applications Claiming Priority (2)
Application Number
Priority Date
Filing Date
Title
GB37320/69A
GB1268865A
(en)
1969-07-29
1969-07-24
THE PREPARATION OF D-THREO-1-p-METHYLSULFONYLPHENYL-2-DICHLOROACETAMIDOPROPANE-1,3-DIOL
FR6925892A
FR2054852A5
(en)
1969-07-29
1969-07-29
Publications (1)
Publication Number
Publication Date
GB1268867A
true
GB1268867A
(en)
1972-03-29
Family
ID=26215193
Family Applications (2)
Application Number
Title
Priority Date
Filing Date
GB4807871A
Expired
GB1268866A
(en)
1969-07-24
1969-07-24
THE PREPARATION OF THREO-RICHbeta-p-METHYLSULPHONYLPHENYL SERINE
GB4811171A
Expired
GB1268867A
(en)
1969-07-24
1969-07-24
THE PREPARATION OF D-THREO-beta-p-METHYLSULPHONYLPHENYLSERINE ESTER
Family Applications Before (1)
Application Number
Title
Priority Date
Filing Date
GB4807871A
Expired
GB1268866A
(en)
1969-07-24
1969-07-24
THE PREPARATION OF THREO-RICHbeta-p-METHYLSULPHONYLPHENYL SERINE
Country Status (1)
Country
Link
GB
(2)
GB1268866A
(en)
Cited By (1)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US4118575A
(en)
*
1974-09-09
1978-10-03
Choay S.A.
Derivatives of para-guanidino-L-phenylalanine and methods of preparing them
Families Citing this family (1)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
CN102617418B
(en)
*
2012-02-21
2014-05-07
山东汉兴医药科技有限公司
Method for recovering amino acid ester from amino acid esterification mother liquor
1969
1969-07-24
GB
GB4807871A
patent/GB1268866A/en
not_active
Expired
1969-07-24
GB
GB4811171A
patent/GB1268867A/en
not_active
Expired
Cited By (1)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US4118575A
(en)
*
1974-09-09
1978-10-03
Choay S.A.
Derivatives of para-guanidino-L-phenylalanine and methods of preparing them
Also Published As
Publication number
Publication date
GB1268866A
(en)
1972-03-29
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