m-Chloroperbenzoic acid → 2-((10S,13S,16R,17R)-17-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

HRID 1186053Notes

Reaction equation

HRID 1186053 reaction equation
[C:1]([O:4][CH2:5]/[C:6](=[C:12]1\[C@H:13]([CH3:32])[CH2:14][CH:15]2[C@:28]\1([CH3:29])[CH2:27][CH:26]=[C:25]1[CH:16]2[CH2:17][CH2:18][C:19]2[C@:24]1([CH3:30])[CH:23]=[CH:22][C:21](=[O:31])[CH:20]=2)/[O:7][Si](C)(C)C)(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:41])C=1>C(Cl)Cl>[C:1]([O:4][CH2:5][C:6]([C@:12]1([OH:41])[C@:28]2([CH3:29])[CH:15]([CH:16]3[C:25](=[CH:26][CH2:27]2)[C@:24]2([CH3:30])[C:19](=[CH:20][C:21](=[O:31])[CH:22]=[CH:23]2)[CH2:18][CH2:17]3)[CH2:14][C@H:13]1[CH3:32])=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59271736(Z)-2-((10S,13S,16R)-10,13,16-trimethyl-3-oxo-7,8,12,13,15,16-hexahydro-3H-cyclopenta[a]phenanthren-17(6H,10H,14H)-ylidene)-2-(trimethylsilyloxy)ethyl acetate

Product 1

HCID 534920572-((10S,13S,16R,17R)-17-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(Z)-2-((10S,13S,16R)-10,13,16-trimethyl-3-oxo-7,8,12,13,15,16-hexahydro-3H-cyclopenta[a]phenanthren-17(6H,10H,14H)-ylidene)-2-(trimethylsilyloxy)ethyl acetate is dissolved in methylene chloride and the mixture is cooled to zero degrees Celsius. A solution of m-chloroperbenzoic acid in methylene chloride is added dropwise and the mixture is stirred for 4 hours. The organic phase was washed with aqueous acetic acid and then aqueous bisulfite. The organic phase was concentrated and chromatographed on silica gel to yield the title compound.

Workup

  1. temperaturethe mixture is cooled to zero degrees Celsius
  2. washThe organic phase was washed with aqueous acetic acid
  3. concentrationThe organic phase was concentrated
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-bf37ba31416345c483ae7bfba43f61c0
Source dataset
uspto-grants-2014_03
Patent number
US08673887B2

Reaction notes

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