Cholesterol → HCID 131722768, compound

HRID 1840231Notes

Reaction equation

HRID 1840231 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 min 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 h and then mixed with an aqueous solution of potassium hydrogensulphate. The phases were separated and the aqueous phase extracted with chloroform. The combined organic phases were washed with aqueous potassium hydrogensulphate and water and dried over 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 h
  3. customThe phases were separated
  4. extractionthe aqueous phase extracted with chloroform
  5. washThe combined organic phases were washed with aqueous potassium hydrogensulphate and water
  6. dry with materialdried over MgSO4
  7. filtrationAfter filtration and evaporation the crude product
  8. customwas chromatographed (silica, chloroform/methanol 99:1)

Sources & evidence

ORD record
ord-6046870ce99e4bacba1f0539fb8766e7
Source dataset
uspto-grants-2004_01
Patent number
US06680047B2

Reaction notes

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