Acetic Acid → 7-[2-(2-Formamidothiazol-4-yl)-2-butoxyiminoacetamido]-3-methoxy-3-cephem-4-carboxylic acid

HRID 1284786Notes

Reaction equation

HRID 1284786 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:37][O:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:10]([NH:12][CH:13]2[C:35](=[O:36])[N:15]3[C:16]([C:22]([O:24]CC4C=CC([N+]([O-])=O)=CC=4)=[O:23])=[C:17]([O:20][CH3:21])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2].O.C(O)(=O)C.CO>[C].[Pd].O1CCCC1>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:37][O:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:10]([NH:12][CH:13]2[C:35](=[O:36])[N:15]3[C:16]([C:22]([OH:24])=[O:23])=[C:17]([O:20][CH3:21])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 962WaterHCID 1317124924-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-butoxyiminoacetamido]-3-methoxy-3-cephem-4-carboxylate

Product 1

HCID 1317124937-[2-(2-Formamidothiazol-4-yl)-2-butoxyiminoacetamido]-3-methoxy-3-cephem-4-carboxylic acidYield 75.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-butoxyiminoacetamido]-3-methoxy-3-cephem-4-carboxylate (syn isomer, 1.7 g.), 10% palladium carbon (1 g.), water (3 ml.), acetic acid (0.3 ml.), methanol (20 ml.) and tetrahydrofuran (35 ml.) was treated in a similar manner to that of Example 15-(2) to give 7-[2-(2-formamidothiazol-4-yl)-2-butoxyiminoacetamido]-3-methoxy-3-cephem-4-carboxylic acid (syn isomer, 1 g.), yellow powder.

Workup

  1. additionwas treated in a similar manner to that of Example 15-(2)

Sources & evidence

ORD record
ord-91ff3d17332341e9a7a44e2efa4e3ba3
Source dataset
uspto-grants-1986_01
Patent number
US04563522

Reaction notes

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