Water → 3beta-Caprylamido-7alpha,12alpha-dihydroxy-5beta-cholan-24-oic methylester

HRID 1934326Notes

Reaction equation

HRID 1934326 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([CH2:36][CH3:37])CC)C.[C:38](Cl)(=[O:44])[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].O>C(Cl)Cl>[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:44])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:36][CH3:37])[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 67340Hexanoyl chlorideHCID 10364902HCID 10364902, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.0 g of 3β-amino-7α,12α-dihydroxy-5β-cholan-24-oic methylester (FIG. 5A-1) [see Example I] were dissolved in 30 ml dry methylene chloride and treated with 15 ml triethyl amine under stirring. 1.2 g of caproyl chloride acid in 10 ml methylene chloride were 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 0.7 g 3β-caprylamido-7α,12α-dihydroxy-5β-cholan-24-oic methylester (FIG. 5A-14).

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-a66d04a977e94e50b0d82ab2c56e7107
Source dataset
uspto-grants-2002_05
Patent number
US06384024B1

Reaction notes

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