m-Chloroperbenzoic acid → 21-Chloro-9-fluoro-11beta,17-dihydroxy-16alpha-[(2-phenyloxiranyl)methoxy]pregna-1,4-diene-3,20-dione

HRID 918381Notes

Reaction equation

HRID 918381 reaction equation
[Cl:1][CH2:2][C:3](=[O:37])[C@:4]1([OH:36])[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@:18]([F:24])([C@@H:19]([OH:23])[CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:25])[CH:14]=[CH:15]2)[CH2:10][CH2:9]3)[CH2:6][C@H:5]1[O:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[CH2:29].ClC1C=CC=C(C(OO)=[O:46])C=1>ClCCl>[Cl:1][CH2:2][C:3](=[O:37])[C@:4]1([OH:36])[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@:18]([F:24])([C@@H:19]([OH:23])[CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:25])[CH:14]=[CH:15]2)[CH2:10][CH2:9]3)[CH2:6][C@H:5]1[O:26][CH2:27][C:28]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:29][O:46]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 8673374521-Chloro-9-fluoro-11beta,17-dihydroxy-16alpha-[(2-phenyl-2-propenyl)oxy]-pregna-1,4-diene-3,20-dione

Product 1

HCID 8673374621-Chloro-9-fluoro-11beta,17-dihydroxy-16alpha-[(2-phenyloxiranyl)methoxy]pregna-1,4-diene-3,20-dioneYield 116.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.0 g of 21-chloro-9-fluoro-11β,17-dihydroxy-16α-[(2-phenyl-2-propenyl)oxy]pregna-1,4-diene-3,20-dione in 100 ml of dichloromethane is stirred with 1.6 g of m-chloroperbenzoic acid for 1 hour at room temperature. The resulting solution is washed with a mixture of 100 ml each of 5% sodium sulfite solution and 5% sodium bicarbonate solution, dried, and evaporated in vacuo to give 4.8 g of crude 21-chloro-9-fluoro-11β,17-dihydroxy-16α-[(2-phenyloxiranyl)methoxy]pregna-1,4-diene-3,20-dione.

Workup

  1. washThe resulting solution is washed with a mixture of 100 ml each of 5% sodium sulfite solution and 5% sodium bicarbonate solution
  2. customdried
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-66d6ed8a770344c49352832daf0e35bf
Source dataset
uspto-grants-1976_07
Patent number
US03971772

Reaction notes

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