Imidazole → HCID 69410951, compound

HRID 1816481Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:30])[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]([OH:27])[C:16]4([CH3:29])[CH3:28])=[CH:10][CH2:9]1)[CH3:7].N1C=CN=C1.[Si:36](Cl)([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:30])[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:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[C:16]4([CH3:29])[CH3:28])=[CH:10][CH2:9]1)[CH3:7]

Participants

Conditions

Temperature: 65 °C

Procedure

3β-Hydroxy-4,4-dimethyl-5α-chola-8,14-dien-24-oic acid methyl ester (18.2 g) is suspended in 400 ml of DMF and 14.8 g of imidazol and 13.0 g of t-butyldimethylsilylchloride is added. The reaction is stirred at 65° C. for 20 hours. After aqueous work-up and crystallization from ether/methanol, 3β-tert-butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24-oic acid methyl ester (21 g) is obtained. Melting point: 124-125° C. 1H-NMR (CDCl3, 400 MHz): δ=5.34 (1H, s); 3.68 (3H, s); 3.2 (1H, m); 0.9 (9H, s); 0.04 (6H, m).

Workup

customAfter aqueous work-up and crystallization from ether/methanol

Sources & evidence

ORD record: ord-1ab8a1b9b9ce43e1b33bcf7e26d1f458
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06884796B2

Reaction notes

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