4-Nitrobenzyl 7-[2-[2-(2,2,2-trifluoroacetamido)thiazol-4-yl]-2-(4-fluorobenzyloxyimino)acetamido]-3-cephem-4-carboxylate → HCID 131712359, compound

HRID 745432Notes

Reaction equation

HRID 745432 reaction equation
[F:1][C:2]([F:48])([F:47])[C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:37][O:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)[C:12]([NH:14][CH:15]2[C:35](=[O:36])[N:17]3[C:18]([C:22]([O:24]CC4C=CC([N+]([O-])=O)=CC=4)=[O:23])=[CH:19][CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1)=[O:4]>O.C(O)(=O)C.O1CCCC1.CO.[C].[Pd]>[F:47][C:2]([F:1])([F:48])[C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:37][O:38][CH2:39][C:40]2[CH:41]=[CH:42][C:43]([F:46])=[CH:44][CH:45]=2)[C:12]([NH:14][CH:15]2[C:35](=[O:36])[N:17]3[C:18]([C:22]([OH:24])=[O:23])=[CH:19][CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1)=[O:4]

Participants

7

Reactant 1

HCID 1317123584-Nitrobenzyl 7-[2-[2-(2,2,2-trifluoroacetamido)thiazol-4-yl]-2-(4-fluorobenzyloxyimino)acetamido]-3-cephem-4-carboxylate

Product 1

HCID 131712359HCID 131712359, compoundYield 83.7%

Reagents, catalysts & solvents 5

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-nitrobenzyl 7-[2-[2-(2,2,2-trifluoroacetamido)thiazol-4-yl]-2-(4-fluorobenzyloxyimino)acetamido]-3-cephem-4-carboxylate (syn isomer, 4.65 g.), 10% palladium carbon (2.3 g) in water (9.3 ml.), acetic acid (0.93 ml.), tetrahydrofuran (93 ml.) and methanol (93 ml.) were treated in a similar manner to that of Exaple 7-(2) to give 7-[2-[2-(2,2,2-trifluoroacetamido)thiazol-4-yl]-2-(4-fluorobenzyloxyimino)-acetamido]-3-cephem-4-carboxylic acid (syn isomer, 3.15 g.).

Workup

  1. additionwere treated in a similar manner to that of Exaple 7-(2)

Sources & evidence

ORD record
ord-85bd59763ae54064be5ab1702f4543cd
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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