GB695769A - Process for the manufacture of d-threo-1-p-nitrophenyl-2-dichloroacetylamino-1,3-propandiol - Google Patents

Process for the manufacture of d-threo-1-p-nitrophenyl-2-dichloroacetylamino-1,3-propandiol

Info

Publication number
GB695769A
GB695769A GB24546/51A GB2454651A GB695769A GB 695769 A GB695769 A GB 695769A GB 24546/51 A GB24546/51 A GB 24546/51A GB 2454651 A GB2454651 A GB 2454651A GB 695769 A GB695769 A GB 695769A
Authority
GB
United Kingdom
Prior art keywords
threo
nitrophenylserine
phenylserine
chloride
product
Prior art date
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
GB24546/51A
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.)
Roche Products Ltd
Original Assignee
Roche Products 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.)
Filing date
Publication date
Application filed by Roche Products Ltd filed Critical Roche Products Ltd
Publication of GB695769A publication Critical patent/GB695769A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Chloramphenicol is manufactured by treating alkyl esters of L-threo-b -p-nitrophenylserine with dichloracetic acid chloride or anhydride followed by selective reduction at the carbalkoxy group. In examples, the ethyl ester of L-threo-b -p-nitrophenylserine is treated with dichloracetyl chloride in methylene chloride in the presence or absence of dimethylaniline, and the N-dichloracetyl derivative is reduced with lithium borohydride. L - Threo - b - p - nitrophenylserine alkyl esters may be prepared by acetylating DL-threo-b -phenylserine at the amino group, forming the quinine salt of the product and fractionally crystallizing it from water, treating the less-soluble fraction with alkali to liberate L-threo-N - acetyl - b - phenylserine, deacetylating and esterifying this product, diacylating the resulting L-threo-b -phenylserine alkyl ester (e.g. with acetyl chloride or acetic anhydride), nitrating the diacyl derivative and hydrolysing and reesterifying the nitrated product.
GB24546/51A 1950-10-27 1951-10-22 Process for the manufacture of d-threo-1-p-nitrophenyl-2-dichloroacetylamino-1,3-propandiol Expired GB695769A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH695769X 1950-10-27

Publications (1)

Publication Number Publication Date
GB695769A true GB695769A (en) 1953-08-19

Family

ID=4529627

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24546/51A Expired GB695769A (en) 1950-10-27 1951-10-22 Process for the manufacture of d-threo-1-p-nitrophenyl-2-dichloroacetylamino-1,3-propandiol

Country Status (1)

Country Link
GB (1) GB695769A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3036094A (en) * 1955-08-08 1962-05-22 Bayer Ag 1-phenyl-2-azidoacylamino-1, 3-propane diols

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3036094A (en) * 1955-08-08 1962-05-22 Bayer Ag 1-phenyl-2-azidoacylamino-1, 3-propane diols

Similar Documents

Publication Publication Date Title
GB639714A (en) Improvements in or relating to the manufacture of 7-dehydrosterol
GB695769A (en) Process for the manufacture of d-threo-1-p-nitrophenyl-2-dichloroacetylamino-1,3-propandiol
GB695170A (en) Method of purifying organic compounds
GB275641A (en) Process for the production of cellulose esters
DE915566C (en) Process for the preparation of N-acylated amino sugars
GB396575A (en) Process for the preparation of a new type of fibrous cellulose ester
GB722594A (en) Improvements in the manufacture of cellulose esters
SU85792A1 (en) The method of obtaining esters by esterification
GB629439A (en) A process for the manufacture of 2:3:4-triaminopyridine
GB1019569A (en) Esters of 1ª‡,2ª‡-methylene-í¸-androstene-3,17ª‰-diol and a process for their manufacture
SU452196A1 (en) Method of producing γ-amino acid acid
GB668994A (en) Process for the purification of adrenalin
GB705370A (en) Method of preparing racemic and levo-rotatory chloramphenicol from 1-acetoxy-3-oxo-3-phenyl-propane
GB568545A (en) Improvements in the production of organic esters of cellulose
GB581157A (en) Improvements in or relating to the production of organic esters of cellulose
GB601184A (en) Improvements in or relating to the preparation of alkyl acylaminocyanoacetates
GB1139150A (en) Improvements in or relating to the continuous esterification of cellulose
GB742034A (en) Improvements in the manufacture of cellulose esters
GB615602A (en) Improvements in and relating to a process for the manufacture of mixed esters of cellulose and of films thereof
FR1360135A (en) Process for the preparation of steroid nitrite ester
GB735731A (en) Improvements in or relating to the n-acylation of 1-phenyl-2-aminopropan-1:3-diol and its derivatives
GB844866A (en) Process for the manufacture of partially acylated polyvinyl alcohol
GB599066A (en) A method of producing starch esters
GB720298A (en) Preparation of ª‰-indolyl-ª‡-oximinopropionic acid
GB455264A (en) Process for the manufacture of esters of polycyclic alcohols