Sodium Hydroxide → HCID 67647092, compound

HRID 962694Notes

Reaction equation

HRID 962694 reaction equation
[C:1]([O:7][CH2:8]I)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].CC(N(C)C)=O.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([NH:27][C:28]([C@H:30]2[CH2:35][CH2:34][C@H:33]3[C@H:36]4[C@H:46]([CH2:47][CH2:48][C@:31]23[CH3:32])[C@:44]2([CH3:45])[C:39]([CH:40]=[C:41]([C:49]([O-:51])=[O:50])[CH2:42][CH2:43]2)=[CH:38][CH2:37]4)=[O:29])([CH3:26])[CH3:25])=[CH:20][CH:19]=1.[Na+].[OH-].[Na+]>C(OCC)(=O)C>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([NH:27][C:28]([C@H:30]2[CH2:35][CH2:34][C@H:33]3[C@H:36]4[C@H:46]([CH2:47][CH2:48][C@:31]23[CH3:32])[C@:44]2([CH3:45])[C:39]([CH:40]=[C:41]([C:49]([O:51][CH2:8][O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[O:50])[CH2:42][CH2:43]2)=[CH:38][CH2:37]4)=[O:29])([CH3:25])[CH3:26])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 31374DimethylacetamideHCID 104401Iodomethyl pivalateHCID 67747343HCID 67747343, compound

Product 1

HCID 67647092HCID 67647092, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1 ml of pivaloyloxymethyl iodide was added, whilst ice-cooling, to 15 ml of a dimethylacetamide solution containing 196 mg of sodium 17β-{N-[1(4-methoxyphenyl)-1-methylethyl]carbamoyl}androsta-3,5-diene-3-carboxylate (prepared by reacting the compound obtained as described in Example 2 with sodium hydroxide in a conventional salification process). The resulting solution was then stirred for 1 hour, whilst ice-cooling, after which it was diluted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure. The resulting residue was subjected to silica gel column chromatography using a gradient elution method, with solutions of from 1 to 3% by volume of acetone in methylene chloride as the eluent, to give 157 mg of the title compound.

Workup

  1. customprepared
  2. customobtained
  3. temperaturecooling
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was then removed by evaporation under reduced pressure
  7. washa gradient elution method

Sources & evidence

ORD record
ord-5575a823e4064d0393d87c06a8675e70
Source dataset
uspto-grants-1998_06
Patent number
US05760025

Reaction notes

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