Ammonia → 3beta-Hydroxy-4,4-dimethyl-5alpha-chola-8,14-dien-24-oic acid amide

HRID 2187271Notes

Reaction equation

[Si]([O:8][C@H:9]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C@@H:11]([CH2:12][CH2:13][C:14]3[C:15]4[C@:26]([CH3:34])([CH2:27][CH2:28][C:29]=32)[C@@H:18]([C@H:19]([CH3:25])[CH2:20][CH2:21][C:22](O)=[O:23])[CH2:17][CH:16]=4)[C:10]1([CH3:36])[CH3:35])(C(C)(C)C)(C)C.[NH3:37].C(O)C.Cl>>[OH:8][C@H:9]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C@@H:11]([CH2:12][CH2:13][C:14]3[C:15]4[C@:26]([CH3:34])([CH2:27][CH2:28][C:29]=32)[C@@H:18]([C@H:19]([CH3:25])[CH2:20][CH2:21][C:22]([NH2:37])=[O:23])[CH2:17][CH:16]=4)[C:10]1([CH3:36])[CH3:35]

Participants

Reactant 3

HCID 222Ammonia

HCID 21887872Ethanol hydrochloride

HCID 694107953beta-Tert-butyidimethylsilyloxy-4,4-dimethyl-5alpha-chola-8,14-dien-24 oic acid

Product 1

HCID 694115183beta-Hydroxy-4,4-dimethyl-5alpha-chola-8,14-dien-24-oic acid amide

Procedure

3β-tert-Butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24 oic acid (1.0 g) is reacted with ammonia and hydrolysed with ethanol/HCl following the procedure outlined in example to give the title compound (147 mg). Melting point: 233-235° C. 1H-NMR (CDCl3, 400 MHz)): δ=5.36 (1H, s); 5.45-5.2 (2H, broad d); 3.25 (1H, m). MS: Calculated: 399.6. Found 399.3.

Sources & evidence

ORD record: ord-476e607a21814ae88af4ab30e3298f45
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06407086B2

Reaction notes

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