HCID 69410951, compound → 3beta-Tert-butyidimethylsilyloxy-4,4-dimethyl-5alpha-chola-8,14-dien-24 oic acid

HRID 1816492Notes

Reaction equation

C[O:2][C:3](=[O:37])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C:11]([C:12]3[CH2:13][CH2:14][C@@H:15]4[C@:20]([C:22]=3[CH2:23][CH2:24]2)([CH3:21])[CH2:19][CH2:18][C@H:17]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[C:16]4([CH3:36])[CH3:35])=[CH:10][CH2:9]1)[CH3:7]>C1COCC1.C(O)C.[OH-].[Na+]>[Si:28]([O:27][C@H:17]1[CH2:18][CH2:19][C@@:20]2([CH3:21])[C@@H:15]([CH2:14][CH2:13][C:12]3[C:11]4[C@:25]([CH3:26])([CH2:24][CH2:23][C:22]=32)[C@@H:8]([C@H:6]([CH3:7])[CH2:5][CH2:4][C:3]([OH:37])=[O:2])[CH2:9][CH:10]=4)[C:16]1([CH3:35])[CH3:36])([C:31]([CH3:34])([CH3:32])[CH3:33])([CH3:30])[CH3:29]

Participants

Conditions

Temperature: 50 °C

Procedure

3β-tert-Butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24-oic acid methyl ester (3.6 g) is dissolved in a mixture of 150 ml of THF, 120 ml of ethanol and 18 ml of 1M sodium hydroxide. The mixture is stirred for 20 hours at room temperature and 2hours at 50° C. After aqueous work-up and crystallisation from ethanol/water, 2.48 g of 3β-tert-butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24-oic acid is isolated.

Workup

customAfter aqueous work-up and crystallisation from ethanol/water

Sources & evidence

ORD record: ord-c51324f28b5f43c98d00064417786fa0
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06884796B2

Reaction notes

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