2-oxo-2-((10S,13S,16R,17S)-10,13,16-trimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethyl acetate → (10S,13S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one

HRID 221200Notes

Reaction equation

HRID 221200 reaction equation
C([O:4][CH2:5][C:6]([C@:8]1([OH:29])[C@:24]2([CH3:25])[CH:11]([CH:12]3[C:21](=[CH:22][CH2:23]2)[C@:20]2([CH3:26])[C:15](=[CH:16][C:17](=[O:27])[CH:18]=[CH:19]2)[CH2:14][CH2:13]3)[CH2:10][C@H:9]1[CH3:28])=[O:7])(=O)C.C(OCC(=O)[C@@H]1[C@]2(C)C(C3C(=CC2)[C@]2(C)C(=CC(=O)CC2)CC3)C[C@H]1C)(=O)C>>[OH:29][C@@:8]1([C:6](=[O:7])[CH2:5][OH:4])[C@:24]2([CH3:25])[CH:11]([CH:12]3[C:21](=[CH:22][CH2:23]2)[C@:20]2([CH3:26])[C:15](=[CH:16][C:17](=[O:27])[CH:18]=[CH:19]2)[CH2:14][CH2:13]3)[CH2:10][C@H:9]1[CH3:28]

Participants

3

Reactant 2

HCID 534920562-oxo-2-((10S,13S,16R,17S)-10,13,16-trimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethyl acetateHCID 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

Product 1

HCID 59271756(10S,13S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one

Procedure

Prepared according to Example 8, Step 2 substituting 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 for 2-oxo-2-((10S,13S,16R,17S)-10,13,16-trimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethyl acetate.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-7c3919e115974a029bb169955e478cfe
Source dataset
uspto-grants-2012_06
Patent number
US08207151B2

Reaction notes

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