Water → HCID 9797673, compound

HRID 1464405Notes

Reaction equation

HRID 1464405 reaction equation
[C:1]([NH:9][C@@H:10]1[C:23](=[O:24])[N:12]2[C:13]([C:19]([O:21][CH3:22])=[O:20])=[C:14]([CH2:17]Cl)[CH2:15][S:16][C@H:11]12)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>C1COCC1>[C:1]([NH:9][C@@H:10]1[C:23](=[O:24])[N:12]2[CH:13]([C:19]([O:21][CH3:22])=[O:20])[C:14](=[CH2:17])[CH2:15][S:16][C@H:11]12)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 69008957HCID 69008957, compound

Product 1

HCID 9797673HCID 9797673, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 48 ml of SmI2 in THF (0.1M), a solution of 0.8 g of methyl 7β-benzoylamino-3chloromethyl-3-cephem -4-carboxylate in 100 ml of dry THF, was added by dropping at -78° 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 96% yield.

Workup

  1. customby dropping at -78° C

Sources & evidence

ORD record
ord-d56fcceff9134337b57b03b9977c5854
Source dataset
uspto-grants-1994_04
Patent number
US05304641

Reaction notes

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