Water → HCID 9797673, compound

HRID 1464404Notes

Reaction equation

HRID 1464404 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]I)[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.C(Cl)Cl>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

5

Reactant 3

HCID 962WaterHCID 6344DichloromethaneHCID 69012538HCID 69012538, compound

Product 1

HCID 9797673HCID 9797673, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 48 ml of a solution of SmI2 in THF (0.1M) a solution of 1 g of methyl 7β-benzoylamino-3-iodomethyl-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. Methylene chloride was added, and the organic phase was separated, washed with brine, dried, and evaporated in vacuo. After column chromatography the title product was isolated in 65% yield.

Workup

  1. customby dropping at -78° C
  2. customthe organic phase was separated
  3. washwashed with brine
  4. customdried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-e2a54c5868ac4b0984bd356d00ab2178
Source dataset
uspto-grants-1994_04
Patent number
US05304641

Reaction notes

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