Hydrochloric Acid → 3beta-Hydroxy-4,4-dimethyl-5alpha-chola-8,14-dien-24-oic acid-N-phenyl Amide

HRID 1764952Notes

Reaction equation

HRID 1764952 reaction equation
[C:1]1([NH:7][C:8](=[O:42])[CH2:9][CH2:10][C@H:11]([C@@H:13]2[C@:30]3([CH3:31])[C:16]([C:17]4[CH2:18][CH2:19][C@@H:20]5[C@:25]([C:27]=4[CH2:28][CH2:29]3)([CH3:26])[CH2:24][CH2:23][C@H:22]([O:32][Si](C(C)(C)C)(C)C)[C:21]5([CH3:41])[CH3:40])=[CH:15][CH2:14]2)[CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>C(O)C>[C:1]1([NH:7][C:8](=[O:42])[CH2:9][CH2:10][C@H:11]([C@@H:13]2[C@:30]3([CH3:31])[C:16]([C:17]4[CH2:18][CH2:19][C@@H:20]5[C@:25]([C:27]=4[CH2:28][CH2:29]3)([CH3:26])[CH2:24][CH2:23][C@H:22]([OH:32])[C:21]5([CH3:41])[CH3:40])=[CH:15][CH2:14]2)[CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 694119823beta-tert-butyldimethylsilyloxy-4,4-dimethyl-5alpha-chola-8,14-dien-24-oic acid-N-phenyl amide

Product 1

HCID 694109183beta-Hydroxy-4,4-dimethyl-5alpha-chola-8,14-dien-24-oic acid-N-phenyl Amide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3β-tert-Butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24-oic acid-N-phenyl amide (50 mg) is dissolved in 5 ml of ethanol, 0.2 ml of 6N hydrogen chloride is added and the mixture is stirred at room temperature overnight. After aqueous work-up and crystallization from methanol the title compound is obtained. (36 mg). H-NMR (CDCl3, 400 MHz): δ=7.53 (2H, d); 7.33 (2H, t); 7.18 (1H, s); 7.12 (1H, t); 5.36 (1H, s); 3.26 (1H, m). MS: Calculated: 475.7. Found: 475.4.

Workup

  1. customAfter aqueous work-up and crystallization from methanol the title compound
  2. customis obtained

Sources & evidence

ORD record
ord-91b56c53cb994ab2842a5a5edbacdc0a
Source dataset
uspto-grants-2007_06
Patent number
USRE039678E1

Reaction notes

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