m-Chloroperbenzoic acid → HCID 88650314, compound

HRID 569136Notes

Reaction equation

HRID 569136 reaction equation
[C:1]([O:7][CH2:8][O:9][C:10]([CH:12]1[N:17]2[C:18](=[O:40])[C@@H:19]([NH:20][C:21](=[O:39])/[C:22](/[C:26]3[N:27]=[C:28]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[S:29][CH:30]=3)=[CH:23]\[CH2:24][CH3:25])[C@H:16]2[S:15][CH:14]=[C:13]1[Cl:41])=[O:11])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].ClC1C=CC=C(C(OO)=[O:50])C=1>ClCCl.C(=O)([O-])O.[Na+]>[C:1]([O:7][CH2:8][O:9][C:10]([C:12]1[N:17]2[C:18](=[O:40])[C@@H:19]([NH:20][C:21](=[O:39])/[C:22](/[C:26]3[N:27]=[C:28]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[S:29][CH:30]=3)=[CH:23]\[CH2:24][CH3:25])[C@H:16]2[S:15](=[O:50])[CH2:14][C:13]=1[Cl:41])=[O:11])(=[O:6])[C:2]([CH3:4])([CH3:3])[CH3:5]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 88649718HCID 88649718, compound

Product 1

HCID 88650314HCID 88650314, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7beta-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-pentenoyl]amino-3-chloro-2-cephem-4-carboxylic acid pivaloyloxymethyl ester (410 mg) in dichloromethane (3 ml) is added dropwise a solution of m-chloroperbenzoic acid (47.4 mg) in dichloromethane (1 ml) with stirring at 0° C. After stirring at the same temperature for 20 minutes, the reaction mixture is diluted with aqueous sodium hydrogen carbonate. The organic layer is separated, washed with water, dried, and concentrated. The resulting residue is purified by silica gel column chromatography to give 7beta-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-pentenoyl]amino-3-chloro-3-cephem-4-carboxylic acid 1-oxide pivaloyloxymethyl ester (135 mg) as crystals.

Workup

  1. stirringAfter stirring at the same temperature for 20 minutes
  2. customThe organic layer is separated
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-94b08299e94e4ab8a363bd9136ce8fc1
Source dataset
uspto-grants-1988_03
Patent number
US04731361

Reaction notes

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