GB1117616A - Process for preparing 1-(p-acetylphenyl)-2-(2,2-dichloroacetamido)-1,3-propanediol - Google Patents

Process for preparing 1-(p-acetylphenyl)-2-(2,2-dichloroacetamido)-1,3-propanediol

Info

Publication number
GB1117616A
GB1117616A GB38053/65A GB3805365A GB1117616A GB 1117616 A GB1117616 A GB 1117616A GB 38053/65 A GB38053/65 A GB 38053/65A GB 3805365 A GB3805365 A GB 3805365A GB 1117616 A GB1117616 A GB 1117616A
Authority
GB
United Kingdom
Prior art keywords
methyl
dioxolan
ethyl ester
phenyl
acetylphenyl
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
GB38053/65A
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.)
Warner Lambert Co LLC
Original Assignee
Warner Lambert Pharmaceutical Co
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 Warner Lambert Pharmaceutical Co filed Critical Warner Lambert Pharmaceutical Co
Publication of GB1117616A publication Critical patent/GB1117616A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/28—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

1 - (p - Acetylphenyl) - 2 - (2,2 - dichloro-acetamido) - 1,3 - propanediol, in D,L - erythro and threo forms is made by reducing an ester of b -(p-acetylphenyl)-serine or its hydrochloride, in which the acetyl group is protected by an ethylenedioxy residue, forming a cyclic acetal, to give the corresponding protected 3-p-acetylphenyl - 2 - amino - propane - 1,3 - diol and acylating the product with a dichloroacetylating agent, the protecting group being previously or subsequently removed. Suitably, a high threo-content or high erythro-content D,L - b - [p - (2 - methyl - 1,3 - dioxolan - 2 - yl) phenyl] serine ethyl ester hydrochloride prepared according to Specification 1,117,617 is reduced with lithium aluminium hydride, the resulting 1 - [p - (2 - methyl - 1,3 - dioxolan - 2 - yl)phenyl] - 2 - amino - 1,3 - propanediol is reacted with methyl dichloroacetate and the N-dichloroacetyl compound obtained is hydrolysed with dilute hydrochloric acid to remove the ethylenedioxy residue. p - (2 - Methyl - 1,3 - dioxolan - 2 - yl) phenyl-serine ethyl ester hydrochloride is made by (A) reacting p-acetylbenzonitrile with ethylene glycol to give p-(2-methyl-1,3-dioxolan-2-yl) benzonitrile, treating with lithium aluminium hydride or lithium triethoxy aluminium hydride to form p-(2-methyl-1,3-dioxolan-2-yl) benzaldehyde, condensing with glycine ethyl ester to give N - [p - (2 - methyl - 1,3 - dioxolan - 2 - yl) benzylidene] - 3 - [p - (2 - methyl - 1,3 - dioxolan- 2 - yl) phenyl] - serine ethyl ester and hydrolysing this with aqueous HCl; (B) condensing p - (2 - methyl - 1,3 - dioxolan - 2 - yl) benzaldehyde with glycine in the presence of a base and esterifying the resulting p-(2-methyl-1,3-dioxolan - 2 - yl) phenylserine or (C) reacting p-acetylbenzaldehyde with glycine ethyl ester and reacting the product with glycol.
GB38053/65A 1964-09-23 1965-09-06 Process for preparing 1-(p-acetylphenyl)-2-(2,2-dichloroacetamido)-1,3-propanediol Expired GB1117616A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US39876564A 1964-09-23 1964-09-23

Publications (1)

Publication Number Publication Date
GB1117616A true GB1117616A (en) 1968-06-19

Family

ID=23576736

Family Applications (2)

Application Number Title Priority Date Filing Date
GB38053/65A Expired GB1117616A (en) 1964-09-23 1965-09-06 Process for preparing 1-(p-acetylphenyl)-2-(2,2-dichloroacetamido)-1,3-propanediol
GB19884/66A Expired GB1117617A (en) 1964-09-23 1965-09-06 Threo-phenylserine ester derivatives

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB19884/66A Expired GB1117617A (en) 1964-09-23 1965-09-06 Threo-phenylserine ester derivatives

Country Status (6)

Country Link
BE (1) BE669982A (en)
BR (1) BR6573383D0 (en)
CH (2) CH465644A (en)
ES (2) ES317686A1 (en)
GB (2) GB1117616A (en)
SE (1) SE322207B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004024060A2 (en) * 2002-09-11 2004-03-25 Astrazeneca Ab Metalloproteinase inhibitors and intermediates for preparation thereof
US8084643B2 (en) 2006-12-13 2011-12-27 Intervet Inc. Water-soluble prodrugs of florfenicol and its analogs

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MXPA04008677A (en) * 2002-03-08 2004-12-06 Schering Plough Ltd Novel florfenicol-type antibiotics.
US8119667B2 (en) 2005-12-29 2012-02-21 Schering-Plough Animal Health Corporation Carbonates of fenicol antibiotics

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004024060A2 (en) * 2002-09-11 2004-03-25 Astrazeneca Ab Metalloproteinase inhibitors and intermediates for preparation thereof
WO2004024060A3 (en) * 2002-09-11 2004-06-24 Astrazeneca Ab Metalloproteinase inhibitors and intermediates for preparation thereof
US8084643B2 (en) 2006-12-13 2011-12-27 Intervet Inc. Water-soluble prodrugs of florfenicol and its analogs

Also Published As

Publication number Publication date
BR6573383D0 (en) 1973-09-11
ES317686A1 (en) 1966-07-01
BE669982A (en) 1966-03-22
ES317685A1 (en) 1966-08-01
CH465644A (en) 1968-11-30
GB1117617A (en) 1968-06-19
SE322207B (en) 1970-04-06
CH465638A (en) 1968-11-30

Similar Documents

Publication Publication Date Title
FI865030A (en) Process for the preparation of a therapeutically useful N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl] -3-methylbutylamine hydrochloride monohydrate
GB1117616A (en) Process for preparing 1-(p-acetylphenyl)-2-(2,2-dichloroacetamido)-1,3-propanediol
ATE7688T1 (en) 2.3-DIALKOXYPROPYLGLYCERYL ETHER, PROCESS FOR THEIR PREPARATION AND COSMETIC COMPOSITION CONTAINING THEM.
ES436565A1 (en) Enzymatic preparation of 6-d-(')-' -amino-' -(p-hydroxyphenylacetamino)penicillin acid
JP2002517381A5 (en)
ES381534A2 (en) A procedure for the preparation of new derivatives of 1-phenyl-2-aminoetanol. (Machine-translation by Google Translate, not legally binding)
SE8103107L (en) PROCEDURE FOR THE PREPARATION OF 4A-ARYL-OCTAHYDRO-1H-2-PYRINDINES
GB1031425A (en) New aralkylamines and their preparation
GB967601A (en) Improvements relating to hydroxylamine derivatives
FR2273762A1 (en) PROCESS FOR IMPROVING THE STABILITY AND SHAPING OF ANHYDROUS SODIUM METASILICATE, AS WELL AS COMPOSITIONS CONTAINING IT, AND PRODUCTS THUS OBTAINED
FR1262598A (en) Process for preparing aldehydes from 1,2-epoxides, in particular of the beta-hydroxyaldehydes type and unsaturated alpha-beta aldehydes, and products obtained
CH360378A (en) Process for the purification of an alkaline hypophosphite solution containing as an impurity an alkaline phosphite
GB1531016A (en) Buti-rosin a derivatives
GB1034490A (en) N-trimethylacetyl-n-phenylalkylsulfamides and phenylcyclopropylsulfamides
JPS53144503A (en) Preparation of aldehyde
KR850008658A (en) Preparation of Bevantool
JPS55111447A (en) Novel 3-amino-4-homoisotwistane derivative
PL310207A1 (en) Nisatidin containing pharmaceutical agent, method of obtaining nisatidin in its specific form and specific form of nisatidin as such
JPS5538836A (en) Epoxy resin curing agent
JPS57200391A (en) 1-(5-oxo-2-hexenyl)3,7-dimethylxanthine
FR2273761A1 (en) PROCESS FOR IMPROVING THE STABILITY AND SHAPING OF ANHYDROUS SODIUM METASILICATE AND OF THE COMPOSITIONS CONTAINING IT, AND PRODUCTS THUS OBTAINED
IL22533A (en) Preparation of acetoacetamides and intermediates in said preparation
AR044103A1 (en) PROCEDURE AND INTERMEDIATE PRODUCTS FOR THE PREPARATION OF COMPOUNDS 19-NOR-STEROIDS HALOGENED IN POSITION 17
FR2000694A1 (en) Process for 2-methylimidazole intermediate for drugs
SU143403A1 (en) The method of obtaining the O-substituted hydroxylamines