Sodium Hydroxide → 3beta-Caprylamido-7alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid

HRID 1934327Notes

Reaction equation

HRID 1934327 reaction equation
C[O:2][C:3](=[O:39])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][C@@H:24]2[OH:27])[C@:20]2([CH3:21])[C@@H:15]([CH2:16][C@@H:17]([NH:28][C:29](=[O:37])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:18][CH2:19]2)[CH2:14][C@H:13]3[OH:38])[CH2:10][CH2:9]1)[CH3:7].[OH-].[Na+]>CO>[C:29]([NH:28][C@H:17]1[CH2:18][CH2:19][C@@:20]2([CH3:21])[C@H:15]([CH2:14][C@@H:13]([OH:38])[C@@H:12]3[C@@H:22]2[CH2:23][C@H:24]([OH:27])[C@@:25]2([CH3:26])[C@H:11]3[CH2:10][CH2:9][C@@H:8]2[C@H:6]([CH3:7])[CH2:5][CH2:4][C:3]([OH:39])=[O:2])[CH2:16]1)(=[O:37])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 865854493beta-Caprylamido-7alpha,12alpha-dihydroxy-5beta-cholan-24-oic methylester

Product 1

HCID 187381223beta-Caprylamido-7alpha,12alpha-dihydroxy-5beta-cholan-24-oic acidYield 82.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.5 g 3β-caprylamido-7α,12α-dihydroxy-5β-cholan-24-oic methylester (FIG. 5A-14) were dissolved in 20 ml methanol, treated with 2 ml 1N sodium hydroxide and left for 24 h at room temperature. The methanol was then distilled off, 10 ml water were added and the reaction mixture was extracted with ethyl acetate. The water fraction was then acidified with diluted hydrogen chloride, resulting in a white precipitate which was washed with water, to give 0.4 g of pure acid (FIG. 5A-15).

Workup

  1. distillationThe methanol was then distilled off
  2. addition10 ml water were added
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. customresulting in a white precipitate which
  5. washwas washed with water

Sources & evidence

ORD record
ord-b04238aa72cc47c7b80f336c682fb2a7
Source dataset
uspto-grants-2002_05
Patent number
US06384024B1

Reaction notes

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