Water → HCID 67821137, compound

HRID 1464407Notes

Reaction equation

HRID 1464407 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 97%

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-3-chloromethyl-3-cephem-4carboxylate 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 produce was isolated in 97% yield.

Workup

  1. customby dropping at -78° C
  2. customAfter the usual work-up and column chromatography, the title produce
  3. customwas isolated in 97% yield

Sources & evidence

ORD record
ord-1b65cb51e3f64a8a8ef6da796d67312c
Source dataset
uspto-grants-1994_04
Patent number
US05304641

Reaction notes

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