Dicyclohexylcarbodiimide → HCID 23387525, compound

HRID 1170675Notes

Reaction equation

HRID 1170675 reaction equation
[Br:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].[C:7]([NH:17][C@H:18]([C:22](O)=[O:23])[CH:19]([CH3:21])[CH3:20])([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.ClCCl>[Br:1][CH2:2][CH:3]([OH:6])[CH2:4][O:5][C:22](=[O:23])[C@H:18]([CH:19]([CH3:20])[CH3:21])[NH:17][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 208273-Bromo-1,2-propanediolHCID 726987N-Carbobenzoxy-L-valine

Product 1

HCID 23387525HCID 23387525, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-bromo-1,2-propanediol (10.85 g, 70 mmole), N-CBz-L-valine (10.05 g, 40 mmole) and DMAP (0.49 g, 4 mmol) in 250 ml dichloromethane was added dropwise a solution of DCC (9.1 g, 44 mmol) in 50 ml dichloromethane at about 10° C. The mixture was stirred for two days at room temperature and then cooled to 5° C. The urethane was filtered and the solution was evaporated under reduced pressure. The product was isolated by silica gel column chromatography. Yield: 8 g

Workup

  1. temperaturecooled to 5° C
  2. filtrationThe urethane was filtered
  3. customthe solution was evaporated under reduced pressure
  4. customThe product was isolated by silica gel column chromatography

Sources & evidence

ORD record
ord-cec09cfb897c4342bd74ea25d23dd041
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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