Water → 3beta-Caprylamido-7alpha,12alpha-dihydroxy-5beta-cholan-24-oic methylester
Reaction equation
[NH2:1][C@H:2]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@H:4]([CH2:5][C@@H:6]([OH:29])[C@@H:7]3[C@@H:22]2[CH2:21][C@H:20]([OH:27])[C@@:19]2([CH3:28])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:18])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:3]1.C(N([CH2:35][CH3:36])CC)C.[C:37](Cl)(=[O:43])[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].O.[CH2:46](Cl)Cl>>[CH3:46][O:16][C:15](=[O:17])[CH2:14][CH2:13][C@H:12]([C@@H:11]1[C@:19]2([CH3:28])[C@H:8]([C@H:7]3[C@H:22]([CH2:21][C@@H:20]2[OH:27])[C@:23]2([CH3:26])[C@@H:4]([CH2:3][C@@H:2]([NH:1][C:37](=[O:43])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:35][CH3:36])[CH2:25][CH2:24]2)[CH2:5][C@H:6]3[OH:29])[CH2:9][CH2:10]1)[CH3:18]Participants
6
Procedure
1.0 g of 3β-amino-7α,12α-dihydroxy-5β-cholan-24-oic Acid (FIG. 5A-15) methylester (FIG. 5A-1) [see Example I] was 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 ehtyl 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
- extractionextracted with methylene chloride
- dry with materialthe organic fraction was then dried over sodium sulfate
- customevaporated to dryness
- customchromatographed over silica gel with a mixture of ehtyl acetate and hexane (6:4 and 8:2)
Sources & evidence
- ORD record
- ord-64d6d38e3663443cb3ee2b5169fcd9f1
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06589946B2
Reaction notes
Loading…