Isopropanol → HCID 70617962, compound

HRID 372866Notes

Reaction equation

HRID 372866 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:44](=[O:45])[N:12]2[CH:13]([C:28]([O:30][CH:31]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:29])[C:14]([CH:17]([O:24][C:25](=[O:27])[CH3:26])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][S:16][C@H:11]12)=[O:8].C(O)(C)C.ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:44](=[O:45])[N:12]2[C:13]([C:28]([O:30][CH:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)=[O:29])=[C:14]([CH:17]([O:24][C:25](=[O:27])[CH3:26])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

5

Reactant 3

HCID 3776Isopropanol2×HCID 70297m-Chloroperbenzoic acidHCID 70617324HCID 70617324, compound

Product 1

HCID 70617962HCID 70617962, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of stereoisomer A of diphenylmethyl 7-(2-thienylacetamido)-3-(α-acetyloxybenzyl)-2-cephem-4-carboxylate (468 mg) in a mixture (10 ml) of methylene chloride and isopropanol (1:1) is added a solution of 80% m-chloroperbenzoic acid (205 mg) in a mixture (2 ml) of methylene chloride and isopropanol (1:1) at 0° C. After 30 minutes, the reaction mixture is diluted with methylene chloride (120 ml), washed with aqueous sodium hydrogen carbonate and water, dried over sodium sulfate, and evaporated. From the residue are obtained the crystalline 1β-oxide and 1α-oxide of the stereoisomer A of diphenylmethyl 7-(2-thienylacetamido)-3-(α-acetyloxybenzyl)-3-cephem-4-carboxylate.

Workup

  1. washwashed with aqueous sodium hydrogen carbonate and water
  2. dry with materialdried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-741ca08d9ae64857af926c872a62cba5
Source dataset
uspto-grants-1978_05
Patent number
US04092474

Reaction notes

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