HCID 69411949, compound → HCID 69410833, compound

HRID 2187265Notes

Reaction equation

HRID 2187265 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C:12]([C:13]3[CH2:14][CH2:15][C@@H:16]4[C@:21]([C:23]=3[CH2:24][CH2:25]2)([CH3:22])[CH2:20][CH2:19][C@H:18]([OH:28])[C:17]4([CH3:30])[CH3:29])=[CH:11][CH2:10]1)[CH3:8])C>C(O)C.[OH-].[Na+]>[OH:28][C@H:18]1[CH2:19][CH2:20][C@@:21]2([CH3:22])[C@@H:16]([CH2:15][CH2:14][C:13]3[C:12]4[C@:26]([CH3:27])([CH2:25][CH2:24][C:23]=32)[C@@H:9]([C@H:7]([CH3:8])[CH2:6][CH2:5][C:4]([OH:31])=[O:3])[CH2:10][CH:11]=4)[C:17]1([CH3:29])[CH3:30]

Participants

4

Reactant 1

HCID 69411949HCID 69411949, compound

Product 1

HCID 69410833HCID 69410833, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

3β-Hydroxy-4,4-dimethyl-5α-chola-8,14-dien-24-oic acid ethyl ester (1.9 g) is suspended in a mixture of 190 ml of 96% ethanol and 63 ml of 1M sodiumhydroxide. The mixture is stirred for 3.5 h at room temperature. After aqueous work-up and crystallization from ethanol/water, the title compound (1.48 g) is isolated. 1H-NMR (CDCl3, 400 MHz): δ=5.36 (1H, s); 3.22 (1H, m); 1.03 (3H, s). 1.01 (3H, s); 0.97 (3H, d); 0.83 (3H, s); 0.81 (3H, s). MS: Calculated: 400.6. Found 400.3.

Workup

  1. customAfter aqueous work-up and crystallization from ethanol/water

Sources & evidence

ORD record
ord-06195bc944394e74b900059a825db820
Source dataset
uspto-grants-2002_06
Patent number
US06407086B2

Reaction notes

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