Water → HCID 67821137, compound

HRID 1464406Notes

Reaction equation

HRID 1464406 reaction equation
[O:1]([CH2:8][C:9]([NH:11][C@@H:12]1[C:33](=[O:34])[N:14]2[C:15]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[O:22])=[C:16]([CH2:19]Cl)[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>C1COCC1>[O:1]([CH2:8][C:9]([NH:11][C@@H:12]1[C:33](=[O:34])[N:14]2[CH:15]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[O:22])[C:16](=[CH2:19])[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 90153482HCID 90153482, compound

Product 1

HCID 67821137HCID 67821137, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 48 ml of SmI2 in THF (0.1M), a solution of 1.1 g of p-methoxybenzyl 7β-phenoxyacetylamino-3chloromethyl -3-cephem-4carboxylate in 100 ml of dry THF, was dropwise added at -20° C. The resulting mixture was allowed to warm to room temperature in 0.5 hours. Water was added, and the mixture stirred for further 0.2 hours at room temperature. After the usual work-up and column chromatography, the title product was isolated in 65% yield.

Sources & evidence

ORD record
ord-5a6997c777eb4a45ab5eb8825776b516
Source dataset
uspto-grants-1994_04
Patent number
US05304641

Reaction notes

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