Cholesterol → HCID 131722768, compound

HRID 1384756Notes

Reaction equation

HRID 1384756 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, compoundYield 97%

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. After phase separation the aqueous phase was extracted with chloroform. The combined organic phases were washed with aqueous potassium hydrogen sulphate and water and dried (MgSO4). After filtration and evaporation the crude product was chromatographed (silica, chloroform/methanol 99:1) to give 1.63 g (97%) of white solid. The structure was confirmed by 1H NMR (500 MHz).

Workup

  1. customtransferred to a flask
  2. stirringThe reaction mixture was stirred for 2 hours
  3. customAfter phase separation the aqueous phase
  4. extractionwas extracted with chloroform
  5. washThe combined organic phases were washed with aqueous potassium hydrogen sulphate and water
  6. dry with materialdried (MgSO4)
  7. filtrationAfter filtration and evaporation the crude product
  8. customwas chromatographed (silica, chloroform/methanol 99:1)

Sources & evidence

ORD record
ord-1125837981da488f9e397ad206fff870
Source dataset
uspto-grants-2001_07
Patent number
US06261537B1

Reaction notes

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