Aniline → 3beta-tert-butyldimethylsilyloxy-4,4-dimethyl-5alpha-chola-8,14-dien-24-oic acid-N-phenyl amide

HRID 2187269Notes

Reaction equation

[Si:1]([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:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CN1CCOCC1.[NH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>ClCCl>[C:45]1([NH:44][C:22](=[O:24])[CH2:21][CH2:20][C@H:19]([C@@H:18]2[C@:26]3([CH3:34])[C:15]([C:14]4[CH2:13][CH2:12][C@@H:11]5[C@:30]([C:29]=4[CH2:28][CH2:27]3)([CH3:33])[CH2:31][CH2:32][C@H:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2])[C:10]5([CH3:36])[CH3:35])=[CH:16][CH2:17]2)[CH3:25])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

Conditions

Temperature: -15 °C

Procedure

3β-tert-Butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24 oic acid (0.50 g) is dissolved in 15 ml of dry dichloromethane. After cooling to −15° C., 0.188 ml of N-methylmorpholine and 0.153 ml of isobutylchloroformiate is added and the mixture is stirred at −15° C. for 20 minutes, whereupon 0.44 ml of aniline is added. The mixture is stirred overnight and the temperature is slowly elevated to room temperature. After aqueous work-up and crystallization from methanol, 3β-tert-butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24-oic acid-N-phenyl amide (0.431 g) is obtained. H-NMR (CDCl3, 400 MHz): δ=7.53 (2H, d); 7.34 (2H, t); 7.17 (1H, s); 7.12 (1H, t); 5.35 (1H, s); 3.21 (1H, m); 0.9 (9H, s); 0.04 (6H, m).

Workup

additionis added
customis slowly elevated to room temperature
customAfter aqueous work-up and crystallization from methanol

Sources & evidence

ORD record: ord-c82fd6d568914e4193923f9132edb003
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06407086B2

Reaction notes

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