ES437809A1 - Improvements introduced in a procedure to prepare a cefalosporine ester. (Machine-translation by Google Translate, not legally binding) - Google Patents

Improvements introduced in a procedure to prepare a cefalosporine ester. (Machine-translation by Google Translate, not legally binding)

Info

Publication number
ES437809A1
ES437809A1 ES437809A ES437809A ES437809A1 ES 437809 A1 ES437809 A1 ES 437809A1 ES 437809 A ES437809 A ES 437809A ES 437809 A ES437809 A ES 437809A ES 437809 A1 ES437809 A1 ES 437809A1
Authority
ES
Spain
Prior art keywords
formula
ester
thio
methyl
acid
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
ES437809A
Other languages
Spanish (es)
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.)
Eli Lilly and Co
Original Assignee
Eli Lilly and 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
Priority claimed from US471527A external-priority patent/US3928333A/en
Priority claimed from US05/471,528 external-priority patent/US3933808A/en
Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of ES437809A1 publication Critical patent/ES437809A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/36—Methylene radicals, substituted by sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/02—Preparation
    • C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

Improvements made to a process for preparing a cephalosporin ester of the formula **(See formula)** wherein R is acetyl, 2-phenoxyacetyl, 2-phenylacetyl, Nt-BOC-phenylglycyl, 2- (2-thienyl) acetyl, 2- (1,2,3,4-tetrazol-1-yl) acetyl, or a radical formula **(See formula)** in which R3 is hydrogen, or C1-C4 alkanoyl; R1 is hydrogen, acetoxy, methylthio, (2-methyl-1,3,4-thiadiazol-5-yl) thio or (1-methyl-1,2,3,4-tetrazol-5-yl) thio; and R2 is C1-C4 alkyl, characterized by reacting an acid of Delta3 cephalosporin of the formula **(See formula)** wherein R and R1 are as defined hereinbefore with a halogenomethyl ester of an alkanolic acid of the formula **(See formula)** where it is defined as herein before; and X is chlorine or bromine, in the presence of a base in an inert solvent at a temperature below 50ºC, and recovering the product, the improvement characterized by adding an equivalent of base, to an equimolar mixture of the acid and the halogenomethyl ester at a rate such that the rate of acid anion generation is approximately equivalent to the rate of esterification; subject to the limitations that when R is Nt-BOC-phenylglycyl, R1 is different from acetoxy, (2-methyl-l, 3,4-thiadiazol-5-yl) thio, or (1-methyl- -1,2, 3,4-tetrazol-5-yl) thio. (Machine-translation by Google Translate, not legally binding)
ES437809A 1974-05-20 1975-05-20 Improvements introduced in a procedure to prepare a cefalosporine ester. (Machine-translation by Google Translate, not legally binding) Expired ES437809A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US471527A US3928333A (en) 1974-05-20 1974-05-20 Process for the preparation of 3 cephalosporin esters
US05/471,528 US3933808A (en) 1974-05-20 1974-05-20 Cephalosporin esters

Publications (1)

Publication Number Publication Date
ES437809A1 true ES437809A1 (en) 1977-04-01

Family

ID=27043469

Family Applications (1)

Application Number Title Priority Date Filing Date
ES437809A Expired ES437809A1 (en) 1974-05-20 1975-05-20 Improvements introduced in a procedure to prepare a cefalosporine ester. (Machine-translation by Google Translate, not legally binding)

Country Status (13)

Country Link
AR (1) AR212321A1 (en)
AT (1) AT340589B (en)
BG (2) BG25228A3 (en)
CH (1) CH601314A5 (en)
CS (1) CS196272B2 (en)
DD (1) DD120446A5 (en)
DK (1) DK221875A (en)
ES (1) ES437809A1 (en)
HU (1) HU170561B (en)
PL (1) PL103490B1 (en)
SE (1) SE421701B (en)
SU (1) SU731899A3 (en)
YU (1) YU125575A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1190897B (en) * 1982-06-29 1988-02-24 Opos Biochimica Srl PROCEDURE FOR THE PREPARATION OF THE 1-ETHOXYCARBONYLOXYETHYL ACID ACID 6- (D (-) - ALPHA AMINOALPHA-PHENYLACETAMIDE) -PENICILLANIC
US4606865A (en) * 1982-09-20 1986-08-19 Astra Lakemedel Aktiebolag Methods for the preparation of α-bromodiethylcarbonate

Also Published As

Publication number Publication date
SE7505741L (en) 1975-11-21
CS196272B2 (en) 1980-03-31
YU125575A (en) 1982-05-31
SE421701B (en) 1982-01-25
HU170561B (en) 1977-07-28
BG25228A3 (en) 1978-08-10
DK221875A (en) 1975-11-21
AT340589B (en) 1977-12-27
PL103490B1 (en) 1979-06-30
ATA381675A (en) 1977-04-15
DD120446A5 (en) 1976-06-12
AR212321A1 (en) 1978-06-30
SU731899A3 (en) 1980-04-30
CH601314A5 (en) 1978-07-14
BG25096A3 (en) 1978-07-12

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