Methanol → 3beta-Ornithyl-cholesterol-dihydrochloride

HRID 1387716Notes

Reaction equation

HRID 1387716 reaction equation
C([N:8](C(OC(C)(C)C)=O)[C@H:9]([C:14]([OH:16])=O)[CH2:10][CH2:11][CH2:12][NH2:13])(OC(C)(C)C)=O.[CH3:24][CH:25]([CH2:27][CH2:28][CH2:29][C@H:30]([C@@H:32]1[C@:50]2([CH3:51])[C@H:35]([C@H:36]3[C@H:47]([CH2:48][CH2:49]2)[C@:45]2([CH3:46])[C:39]([CH2:40][C@H:41]([CH2:43][CH2:44]2)[OH:42])=[CH:38][CH2:37]3)[CH2:34][CH2:33]1)[CH3:31])[CH3:26].C1CCC(N=C=NC2CCCCC2)CC1.CO.[Cl:69]CCl>CN(C1C=CN=CC=1)C>[ClH:69].[ClH:69].[NH2:8][C@H:9]([C:14]([C@@:41]1([OH:42])[CH2:43][CH2:44][C@@:45]2([CH3:46])[C:39](=[CH:38][CH2:37][C@@H:36]3[C@@H:47]2[CH2:48][CH2:49][C@@:50]2([CH3:51])[C@H:35]3[CH2:34][CH2:33][C@@H:32]2[C@H:30]([CH3:31])[CH2:29][CH2:28][CH2:27][CH:25]([CH3:26])[CH3:24])[CH2:40]1)=[O:16])[CH2:10][CH2:11][CH2:12][NH2:13]

Participants

7

Reactant 5

HCID 887MethanolHCID 5997CholesterolHCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 18638603Di-boc-ornithine

Product 1

HCID 1317228203beta-Ornithyl-cholesterol-dihydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

997 mg (3 mmol) of di-BOC-ornithine was dissolved in 40 ml of dichloromethane. 1.16 g (3 mmol) of cholesterol, 640 mg (3.1 mmol) of DCC, and 50 mg of DMAP were added, and the mixture was stirred at room temperature for 24 h. The dicyclohexylurea precipitate was removed by filtration, the solvent removed in vacuo and the residual solid was recrystallized from 5 ml of hexane yielding 1.62 g (77%) of 3β-BOC-ornithyl-cholesterol as a colorless, crystalline solid. 190 mg (0.27 mmol) of 3β-di-BOC-ornithyl-cholesterol was treated with 6 ml of MeOH (10 mmol HCl) and was stirred at ambient temperature for 1 h. Subsequent removal of the solvent under high vacuum yielded 146 mg (94%) of 3β-ornithyl-cholesterol-dihydrochloride VI as a colorless solid.

Workup

  1. customThe dicyclohexylurea precipitate was removed by filtration
  2. customthe solvent removed in vacuo
  3. customthe residual solid was recrystallized from 5 ml of hexane yielding 1.62 g (77%) of 3β-BOC-ornithyl-cholesterol as a colorless, crystalline solid
  4. stirringwas stirred at ambient temperature for 1 h
  5. customSubsequent removal of the solvent under high vacuum

Sources & evidence

ORD record
ord-d488e722ea154d63b0ce57bb04cf8d3a
Source dataset
uspto-grants-2001_07
Patent number
US06268516B1

Reaction notes

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