Tert-Butylamine → 3beta-Hydroxy-4,4-dimethyl-5alpha-chola-8,14-dien-24-oic acid-N-tert-butylamide

HRID 2187279Notes

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]([OH:24])=O)[CH2:17][CH:16]=4)[C:10]1([CH3:36])[CH3:35])(C(C)(C)C)(C)C.[C:37]([NH2:41])([CH3:40])([CH3:39])[CH3:38].Cl.C(O)C>>[C:37]([NH:41][C:22](=[O:24])[CH2:21][CH2:20][C@H:19]([C@@H:18]1[C@:26]2([CH3:34])[C:15]([C:14]3[CH2:13][CH2:12][C@@H:11]4[C@:30]([C:29]=3[CH2:28][CH2:27]2)([CH3:33])[CH2:31][CH2:32][C@H:9]([OH:8])[C:10]4([CH3:35])[CH3:36])=[CH:16][CH2:17]1)[CH3:25])([CH3:40])([CH3:39])[CH3:38]

Participants

Reactant 3

HCID 6385Tert-Butylamine

HCID 21887872Ethanol hydrochloride

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

Product 1

HCID 694115243beta-Hydroxy-4,4-dimethyl-5alpha-chola-8,14-dien-24-oic acid-N-tert-butylamide

Procedure

3β-tert-Butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24-oic acid (0.50 g) is reacted with tert-butylamine and hydrolysed with HCl/ethanol following the procedure outlined in example 39 to give the title compound (204 mg). Melting point: 171-176° C.

Sources & evidence

ORD record: ord-44d91aa7cb7747fe981e092e5915fd8a
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06407086B2

Reaction notes

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