Sodium Hydroxide → (3beta,5beta,7alpha,12alpha)-7,12-Dihydroxy-3-((1-oxoeicosyl)amino)cholan-24-oic acid

HRID 1357051Notes

Reaction equation

HRID 1357051 reaction equation
C[O:2][C:3](=[O:51])[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:49])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[CH2:18][CH2:19]2)[CH2:14][C@H:13]3[OH:50])[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:50])[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:51])=[O:2])[CH2:16]1)(=[O:49])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86585448HCID 86585448, compound

Product 1

HCID 18738120(3beta,5beta,7alpha,12alpha)-7,12-Dihydroxy-3-((1-oxoeicosyl)amino)cholan-24-oic acidYield 142.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.5 g 3β-arachidylamido-7α,12α-dihydroxy-5β-cholan-24-oic methylester (FIG. 5A-4) 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 0.7 g of the pure 3β-arachidylamido-7α,12α-dihydroxy-5β-cholan-24-oic acid (FIG. 5A-5).

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-f15f7d4681944db3bd0859cf9c958b35
Source dataset
uspto-grants-2003_07
Patent number
US06589946B2

Reaction notes

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