Acetic Anhydride → HCID 69411787, compound

HRID 2187283Notes

Reaction equation

HRID 2187283 reaction equation
[Si]([O:8][C@H:9]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@@H:11]([CH2:12][CH2:13][C:14]3[C:15]4[C@:25]([CH3:33])([CH2:26][CH2:27][C:28]=32)[C@@H:18]([C@H:19]([CH3:24])[CH2:20]CCO)[CH2:17][CH:16]=4)[C:10]1([CH3:35])[CH3:34])(C(C)(C)C)(C)C.[C:36]([O:39][C:40](=O)[CH3:41])(=[O:38])[CH3:37]>N1C=CC=CC=1>[CH3:35][C:10]1([CH3:34])[C@@H:9]([OH:8])[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@H:11]1[CH2:12][CH2:13][C:14]1[C:15]3[C@:25]([CH3:33])([CH2:26][CH2:27][C:28]=12)[C@@H:18]([C@H:19]([CH3:24])[CH2:20][CH2:41][CH2:40][O:39][C:36](=[O:38])[CH3:37])[CH2:17][CH:16]=3

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 69411676HCID 69411676, compound

Product 1

HCID 69411787HCID 69411787, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3β-tert-Butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24-ol (150 mg) is acetylated in a mixture of 2 ml of pyridine and 1 ml of acetic anhydride. The tert-butyldimethylsilyl protecting group is split of by treatment with tetra-butylammonium fluoride hydrate according to the procedure outlined in example 2. After column chromatography and crystallisation from acetone/water, the title compound (36 mg) is obtained. 1H-NMR (CDCl3, 300 MHz): δ=5.35 (1H, s); 4.05 (2H, m); 3.23 (1H, m); 2.04 (3H, s). MS: Calculated: 428.7. Found 428.3.

Workup

  1. customThe tert-butyldimethylsilyl protecting group is split of by treatment with tetra-butylammonium fluoride hydrate according to the procedure
  2. customAfter column chromatography and crystallisation from acetone/water

Sources & evidence

ORD record
ord-84f876a794f14b2da3a942deb510783b
Source dataset
uspto-grants-2002_06
Patent number
US06407086B2

Reaction notes

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