Prenderol → HCID 53986985, compound

HRID 1790799Notes

Reaction equation

HRID 1790799 reaction equation
[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][CH3:7])[CH2:4][OH:5])[CH3:2].[CH2:10]([O:17][C:18]([NH:20][C@H:21]([C:25](O)=[O:26])[CH:22]([CH3:24])[CH3:23])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[CH2:10]([O:17][C:18]([NH:20][C@H:21]([C:25]([O:5][CH2:4][C:3]([CH2:6][CH3:7])([CH2:1][CH3:2])[CH2:8][OH:9])=[O:26])[CH:22]([CH3:24])[CH3:23])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 8284PrenderolHCID 10868DicyclohexylcarbodiimideHCID 726987N-Carbobenzoxy-L-valine

Product 1

HCID 53986985HCID 53986985, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a cooled solution of 2-ethyl-2-hydroxymethyl-butan-1-ol (33.1 g, 250 mmole), 4-dimethylaminopyridine (1.22 g, 10 mmole) and N-benzyloxycarbonyl-L-valine (12.6 g, 50 mmole) in 350 ml dichloromethane was added dropwise a solution of dicyclohexyl-carbodiimide (12.4 g, 60 mmole) in 50 ml dichloromethane. The mixture was stirred 2 days at room temperature and cooled. The urethane was filtered and the solution evaporated under reduced pressure. 350 ml ethyl acetate was added and the organic phase was washed twice with 5% acetic acid, 5% sodium-hydrogencarbonate and water. The organic phase was dried with sodium sulfat and evaporated under reduced pressure. The product was isolated by silica gel column chromatography with dichloromethane/methanol. Yield: 16.4 g=90%.

Workup

  1. temperaturecooled
  2. filtrationThe urethane was filtered
  3. customthe solution evaporated under reduced pressure
  4. addition350 ml ethyl acetate was added
  5. washthe organic phase was washed twice with 5% acetic acid, 5% sodium-hydrogencarbonate and water
  6. dry with materialThe organic phase was dried with sodium sulfat
  7. customevaporated under reduced pressure
  8. customThe product was isolated by silica gel column chromatography with dichloromethane/methanol

Sources & evidence

ORD record
ord-148fd3d2081f40a0ab81c04f4766a0e1
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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