Benzyl Alcohol → HCID 15342788, compound

HRID 863740Notes

Reaction equation

HRID 863740 reaction equation
[N:1]1([C:14]([O:16][CH2:17][CH:18]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]3[C:19]2=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:15])[CH2:13][C@H:7]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[CH2:31](O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C)C1C=CN=CC=1.ClCCl>[N:1]1([C:14]([O:16][CH2:17][CH:18]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]3[C:19]2=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:15])[CH2:13][C@H:7]([O:8][C:9]([CH3:11])([CH3:12])[CH3:10])[CH2:6][C@H:2]1[C:3]([O:5][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:4]

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 978347122996-47-8

Product 1

HCID 15342788HCID 15342788, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

65 mmol of N,N-dicyclohexylcarbodiimide are added to a mixture containing 61 mmol of Fmoc-Hyp(tBu)-OH, 65 mmol of benzyl alcohol and 27 mmol of 4-dimethylaminopyridine in 150 ml of dichloromethane cooled on an ice bath. After one hour at 0° C., the mixture is adjusted to room temperature and left stirring for 18 hours. The dicyclohexylurea precipitate is filtered and the filtrate is evaporated. The residual oil is taken up in ethyl acetate. The solution is washed with 5% sodium bicarbonate, with 5% citric acid and then with a saturated sodium chloride solution. After drying and evaporation, the expected product is obtained in the form of an oil.

Workup

  1. temperaturecooled on an ice bath
  2. customis adjusted to room temperature
  3. waitleft
  4. filtrationThe dicyclohexylurea precipitate is filtered
  5. customthe filtrate is evaporated
  6. washThe solution is washed with 5% sodium bicarbonate, with 5% citric acid
  7. customAfter drying
  8. customevaporation

Sources & evidence

ORD record
ord-805096764c0c4cd0bfbf5db670f58b7b
Source dataset
uspto-grants-1996_10
Patent number
US05561113

Reaction notes

Loading…