Diethyl Ether → HCID 131715367, compound

HRID 256452Notes

Reaction equation

HRID 256452 reaction equation
[CH:1]([NH:3][C:4]1[S:5][C:6]([Br:40])=[C:7]([C:9](=[N:37][O:38][CH3:39])[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])=[CH:17][CH:18]([O:20][CH3:21])[S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2].C(OCC)C.C(OC(C)C)(C)C>O1CCCC1.CO>[CH:1]([NH:3][C:4]1[S:5][C:6]([Br:40])=[C:7]([C:9](=[N:37][O:38][CH3:39])[C:10]([NH:12][CH:13]2[C:35](=[O:36])[N:15]3[C:16]([C:22]([OH:24])=[O:23])=[CH:17][CH:18]([O:20][CH3:21])[S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 7914Diisopropyl EtherHCID 131715366HCID 131715366, compound

Product 1

HCID 131715367HCID 131715367, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-nitrobenzyl 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-2-methoxy-3-cephem-4-carboxylate (syn isomer, 2.9 g.) in a mixture of tetrahydrofuran (110 ml.) and methanol (80 ml.) was treated in a similar manner to that of Example 8-(2) (diethyl ether was used for pulverization instead of diisopropyl ether) to give 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-2-methoxy-3-cephem-4-carboxylic acid (syn isomer, 1.2 g.).

Sources & evidence

ORD record
ord-6ff1688fcf30457f9bc6245d1bc546b2
Source dataset
uspto-grants-1987_10
Patent number
US04703046

Reaction notes

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