Sodium Methoxide → HCID 59271745, compound

HRID 58021Notes

Reaction equation

HRID 58021 reaction equation
[OH:1][CH2:2][C:3]([C:5]1([CH3:26])[C:21]2([CH3:22])[CH:8]([CH:9]3[C:18](=[CH:19][CH2:20]2)[C:17]2([CH3:23])[C:12](=[CH:13][C:14](=[O:24])[CH2:15][CH2:16]2)[CH2:11][CH2:10]3)[CH2:7][CH:6]1[CH3:25])=[O:4].C(OCC(=O)[C@]1(C)[C@]2(C)C(C3C(=CC2)[C@]2(C)C(=CC(=O)CC2)CC3)C[C@H]1C)(=O)C.C[O-].[Na+]>CO>[OH:1][CH2:2][C:3]([C@:5]1([CH3:26])[C@:21]2([CH3:22])[CH:8]([CH:9]3[C:18](=[CH:19][CH2:20]2)[C@:17]2([CH3:23])[C:12](=[CH:13][C:14](=[O:24])[CH2:15][CH2:16]2)[CH2:11][CH2:10]3)[CH2:7][C@H:6]1[CH3:25])=[O:4]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 59271735HCID 59271735, compoundHCID 72266819HCID 72266819, compound

Product 1

HCID 59271745HCID 59271745, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10S,13S,16R,17S)-17-(2-hydroxyacetyl)-10,13,16,17-tetramethyl-6,7,8,10,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one: 2-oxo-2-((10S,13S,16R,17S)-10,13,16,17-tetramethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethyl acetate (144 g) is stirred in 1500 ml methanol and treated with sodium methoxide (25%, 5 ml) for 30 minutes. The mixture is partitioned between methylene chloride and sodium bicarbonate. The organic phase is separated and washed with sodium bicarbonate, dried over sodium sulfate, and concentrated to give the title compound.

Workup

  1. customThe mixture is partitioned between methylene chloride and sodium bicarbonate
  2. customThe organic phase is separated
  3. washwashed with sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9c957cb1185940138852f36f2ac6ed2c
Source dataset
uspto-grants-2016_09
Patent number
US09434758B2

Reaction notes

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