Cholesterol → HCID 131722768, compound

HRID 1384765Notes

Reaction equation

HRID 1384765 reaction equation
CC(C)N=C=NC(C)C.[NH:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:12][C:13]([OH:15])=[O:14].[CH3:23][CH:24]([CH2:26][CH2:27][CH2:28][C@H:29]([C@@H:31]1[C@:49]2([CH3:50])[C@H:34]([C@H:35]3[C@H:46]([CH2:47][CH2:48]2)[C@:44]2([CH3:45])[C:38]([CH2:39][C@H:40]([CH2:42][CH2:43]2)[OH:41])=[CH:37][CH2:36]3)[CH2:33][CH2:32]1)[CH3:30])[CH3:25].S([O-])(O)(=O)=O.[K+]>ClCCl.CN(C1C=CN=CC=1)C>[CH3:25][CH:24]([CH2:26][CH2:27][CH2:28][C@H:29]([C@@H:31]1[C@:49]2([CH3:50])[C@H:34]([C@H:35]3[C@H:46]([CH2:47][CH2:48]2)[C@:44]2([CH3:45])[C:38]([CH2:39][C@H:40]([CH2:42][CH2:43]2)[OH:41])=[CH:37][CH2:36]3)[CH2:33][CH2:32]1)[CH3:30])[CH3:23].[C:16]([NH:10][CH2:11][CH2:12][C:13]([O-:15])=[O:14])([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17]

Participants

7

Reactant 4

HCID 5997CholesterolHCID 12734DiisopropylcarbodiimideHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 516920Potassium bisulfate

Product 1

HCID 131722768HCID 131722768, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

DIC (510 μl) was added to a solution of Boc-β-Ala-OH (1.25 g, 6.60 mmol) in dichloromethane (15 ml) under an inert atmosphere. The reaction mixture was stirred for 30 minutes and then transferred to a flask containing a solution of cholesterol (1.16 g, 3.00 mmol) and DMAP (367 mg, 3.00 mmol) in dichloromethane (15 ml). The reaction mixture was stirred for 2 hours and then poured onto an aqeous solution of potassium hydrogen sulphate.

Workup

  1. customtransferred to a flask
  2. stirringThe reaction mixture was stirred for 2 hours

Sources & evidence

ORD record
ord-f92996c859a74853acbe2154d3255ec7
Source dataset
uspto-grants-2001_07
Patent number
US06261537B1

Reaction notes

Loading…