Water → HCID 86585448, compound

HRID 1357050Notes

Reaction equation

HRID 1357050 reaction equation
[CH3:1][O:2][C:3](=[O:30])[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]([NH2:28])[CH2:18][CH2:19]2)[CH2:14][C@H:13]3[OH:29])[CH2:10][CH2:9]1)[CH3:7].C(N(CC)CC)C.[C:38](Cl)(=[O:58])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57].O>CN(C)C=O>[CH3:1][O:2][C:3](=[O:30])[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:38](=[O:58])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:18][CH2:19]2)[CH2:14][C@H:13]3[OH:29])[CH2:10][CH2:9]1)[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 9862365Eicosanoyl chlorideHCID 10364902HCID 10364902, compound

Product 1

HCID 86585448HCID 86585448, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.0 g of 3β-amino-7α,12α-dihydroxy-5β-cholan-24-oic methylester (FIG. 5A-1) [see Example I] was dissolved in 30 ml dry dimethylformamide and treated with 15 ml triethyl amine under stirring. 1.0 g of arachidoyl chloride in 10 ml dimethylformamide was added dropwise to the resulting solution, and the stirring was continued overnight. The reaction mixture was poured into water, extracted with methylene chloride, the organic fraction was then dried over sodium sulfate, evaporated to dryness and chromatographed over silica gel with a mixture of ethyl acetate and hexane (6:4 and 8:2), to give 0.6 g 3β-arachidylamido-7α,12α-dihydroxy-5β-cholan-24-oic methylester (FIG. 5A-4).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialthe organic fraction was then dried over sodium sulfate
  3. customevaporated to dryness
  4. customchromatographed over silica gel with a mixture of ethyl acetate and hexane (6:4 and 8:2)

Sources & evidence

ORD record
ord-b334f96de1bb422a8ef5950f57b46ac3
Source dataset
uspto-grants-2003_07
Patent number
US06589946B2

Reaction notes

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