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

HRID 918373Notes

Reaction equation

HRID 918373 reaction equation
[Cl:1][CH2:2][C:3](=[O:32])[C@:4]1([OH:31])[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]([CH3:30])=[CH2:29].ClC1C=CC=C(C(OO)=[O:41])C=1>ClCCl>[Cl:1][CH2:2][C:3](=[O:32])[C@:4]1([OH:31])[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([CH3:30])[CH2:29][O:41]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 8673373921-Chloro-9-fluoro-11beta,17-dihydroxy-16alpha-((2-methyl-2-propenyl)oxy)pregna-1,4,diene-3,20-dione

Product 1

HCID 8673374121-Chloro-9-fluoro-11beta,17-dihydroxy-16alpha-[(2-methyloxiranyl)methoxy]pregna-1,4-diene-3,20-dioneYield 14.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.0 g of 21-chloro-9-fluoro-11β,17-dihydroxy-16α-[ (2-methyl-2-propenyl)oxy]pregna-1,4-diene-3,20-dione in 100 ml of dichloromethane is stirred with 1.4 g of m-chloroperbenzoic acid for 210 minutes. The solution is washed with a mixture of 10% potassium carbonate solution and 10% sodium sulfite solution, dried, and evaporated in vacuo to give an oil which solidifies on standing. Recrystallization from acetone-hexane gives 1.94 g as a first crop, and 820 mg as a second crop. Recrystallization of 600 mg of crop 1 from acetone-hexane gives 460 mg of 21-chloro-9-fluoro-11β,17-dihydroxy-16α-[(2-methyloxiranyl)methoxy]pregna-1,4-diene-3,20-dione, melting point 193°-236°C.

Workup

  1. washThe solution is washed with a mixture of 10% potassium carbonate solution and 10% sodium sulfite solution
  2. customdried
  3. customevaporated in vacuo
  4. customto give an oil which
  5. customRecrystallization from acetone-hexane
  6. customgives 1.94 g as a first crop, and 820 mg as a second crop
  7. customRecrystallization of 600 mg of crop 1 from acetone-hexane

Sources & evidence

ORD record
ord-88b51c8ac8c84026aecbdb9167f55f69
Source dataset
uspto-grants-1976_07
Patent number
US03971772

Reaction notes

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