Potassium Hydroxide → HCID 86741339, compound

HRID 1905850Notes

Reaction equation

HRID 1905850 reaction equation
C([O:3][C@@H:4]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C@H:6]([CH2:7][C:8](=[O:38])[C@@H:9]3[C@@H:29]2[CH2:28][C@H:27]([O:34]C=O)[C@@:26]2([CH3:37])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:25])[CH2:15][CH2:16][C:17]([NH:19][C:20]([CH3:24])([CH3:23])[CH2:21][OH:22])=[O:18])[CH2:5]1)=O.[OH-].[K+]>>[OH:3][C@@H:4]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C@H:6]([CH2:7][C:8](=[O:38])[C@@H:9]3[C@@H:29]2[CH2:28][C@H:27]([OH:34])[C@@:26]2([CH3:37])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:25])[CH2:15][CH2:16][C:17]([NH:19][C:20]([CH3:24])([CH3:23])[CH2:21][OH:22])=[O:18])[CH2:5]1

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 13799233HCID 13799233, compound

Product 1

HCID 86741339HCID 86741339, compound

Procedure

The diformyl amide obtained in Example 2 (2 g) was hydrolyzed with 5% methanolic KOH (reflux, 1 hr). Dilution with water and extraction with ethyl acetate gave chromatographically pure 2-(3α,12α-dihydroxy-7-oxo-5β-cholan-24-amido)-2-methyl-1-propanol which was recrystallized from ethyl acetate (colorless prisms), melting at 229°-231° C. PMR (δ ppm): 0.70 (3H, s, 18--CH3), 1.09 (3H, d, J=6 Hz, 21--CH3), 1.16 (3H, s, 19--CH3), 1.52 (6H, s, --C(CH3)2 --), 3.65 (1H, m, 3β--H), 3.86 (2H, s, --CH2OH), 4.09 (1H, m, 12β--H), 7.54 (1H, s, --NH--).

Workup

  1. extractionDilution with water and extraction with ethyl acetate

Sources & evidence

ORD record
ord-6f76a6fa506642309c3ab6eaa1aaf592
Source dataset
uspto-grants-1987_03
Patent number
US04648995

Reaction notes

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