Hydrochloric Acid → 3beta-hydroxy-4,4-dimethyl-5alpha-chola-8,14-dien-24-oic acid-N,N-dimethyl amide

HRID 479308Notes

Reaction equation

HRID 479308 reaction equation
[CH3:1][N:2]([CH3:38])[C:3](=[O:37])[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](C(C)(C)C)(C)C)[C:16]4([CH3:36])[CH3:35])=[CH:10][CH2:9]1)[CH3:7].Cl>C(O)C>[CH3:38][N:2]([CH3:1])[C:3](=[O:37])[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([CH3:36])[CH3:35])=[CH:10][CH2:9]1)[CH3:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317242073beta-tert-butyidimethylsilyloxy-4,4-dimethyl-5alpha-chola-8,14-dien-24 oic acid-N,N-dimethyl amide

Product 1

HCID 698734753beta-hydroxy-4,4-dimethyl-5alpha-chola-8,14-dien-24-oic acid-N,N-dimethyl amideYield 74.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3β-tert-butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24 oic acid-N,N-dimethyl amide (0.10 g) is dissolved in 5 ml of ethanol, 0.2 ml of 6N hydrogen chloride is added and the mixture is stirred at room temperature the weekend over. The product is precipitated with 10 ml of water, filtered and recrystallized from ethanol/heptan to give the title compound (59 mg). M.p. 192-195° C. 1H-NMR (CDCl3, 400 MHz)): δ=5.36 (1H, s); 3.24 (1H, m); 3.02 (3H, s); 2.94 (3H, s). Molecular weight: Calculated: 427.7. Found (by mass spectroscopy): 427.4.

Workup

  1. customThe product is precipitated with 10 ml of water
  2. filtrationfiltered
  3. customrecrystallized from ethanol/heptan

Sources & evidence

ORD record
ord-122076c1b7e04bcdb55181df9e073bd4
Source dataset
uspto-grants-2003_11
Patent number
US06645953B2

Reaction notes

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