Methanol → HCID 86761364, compound

HRID 1014982Notes

Reaction equation

HRID 1014982 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@:36]2([CH3:37])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:35]2[CH2:34][CH2:33][C@@:32]2([CH3:38])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[C@@H:21]([O:23][CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])[CH3:22])[CH2:12][C@@H:11]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CO.C[O-].[Na+].O>O1CCCC1.C(OCC)(=O)C>[Si:1]([O:8][C@@H:9]1[C@@:36]2([CH3:37])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:35]2[CH2:34][CH2:33][C@@:32]2([CH3:38])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[C@@H:21]([O:23][CH2:24][C:25]([OH:27])=[O:26])[CH3:22])[CH2:12][C@@H:11]([O:39][Si:40]([C:43]([CH3:44])([CH3:46])[CH3:45])([CH3:41])[CH3:42])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 10942334Sodium MethoxideHCID 86761363HCID 86761363, compound

Product 1

HCID 86761364HCID 86761364, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl [{1α,3β-bis(tert-butyldimethylsilyloxy)pregna-5,7-dien-20(S)-yl}oxy]acetate (9 mg, 0.013 mmol) in tetrahydrofuran (0.13 ml), a 1M methanol solution of sodium methoxide (0.13 ml) was added and stirred at room temperature for 20 minutes. Water (0.26 ml) was further added and stirred at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium dihydrogenphosphate, and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the titled compound (6 mg, 73%) as a colorless solid.

Workup

  1. stirringstirred at room temperature for 30 minutes
  2. washwashed with saturated aqueous sodium dihydrogenphosphate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fa986a390dee44c5964b563b7142136a
Source dataset
uspto-grants-2011_07
Patent number
US07985744B2

Reaction notes

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