m-Chloroperbenzoic acid → 21-Chloro-11beta,17-dihydroxy-16alpha-(oxiranylmethoxy)-pregn-4-ene-3,20-dione

HRID 918414Notes

Reaction equation

HRID 918414 reaction equation
[CH2:1]([O:4][C@@H:5]1[CH2:25][C@@H:24]2[C@:11]([CH3:29])([CH2:12][C@H:13]([OH:28])[C@H:14]3[C@H:23]2[CH2:22][CH2:21][C:20]2[C@:15]3([CH3:27])[CH2:16][CH2:17][C:18](=[O:26])[CH:19]=2)[C@@:6]1([OH:30])[C:7](=[O:10])[CH2:8][Cl:9])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:39])C=1>ClCCl>[Cl:9][CH2:8][C:7](=[O:10])[C@:6]1([OH:30])[C@:11]2([CH3:29])[C@H:24]([C@H:23]3[C@H:14]([C@@H:13]([OH:28])[CH2:12]2)[C@:15]2([CH3:27])[C:20](=[CH:19][C:18](=[O:26])[CH2:17][CH2:16]2)[CH2:21][CH2:22]3)[CH2:25][C@H:5]1[O:4][CH2:1][CH:2]1[CH2:3][O:39]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 8673375816alpha-Allyloxy-21-chloro-11beta,17-dihydroxypregn-4-ene-3,20-dione

Product 1

HCID 8673375921-Chloro-11beta,17-dihydroxy-16alpha-(oxiranylmethoxy)-pregn-4-ene-3,20-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 16α-allyloxy-21-chloro-11β,17-dihydroxypregn-4-ene-3,20-dione (3.8 mmoles) in 50 ml of dichloromethane is stirred with 0.76 g of m-chloroperbenzoic acid for 19 hours at room temperature. The resulting solution is washed with a mixture of 10% potassium carbonate solution and 10% sodium sulfite solution, dried, and evaporated in vacuo to yield the title compound.

Workup

  1. washThe resulting solution is washed with a mixture of 10% potassium carbonate solution and 10% sodium sulfite solution
  2. customdried
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-a24a56dc051e4600a2927377faeb7af1
Source dataset
uspto-grants-1976_07
Patent number
US03971773

Reaction notes

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