Dicyclohexylcarbodiimide → HCID 53733618, compound

HRID 1790744Notes

Reaction equation

HRID 1790744 reaction equation
[OH:1][C@@H:2]([CH3:15])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:4].[C:16]([NH:26][C@H:27]([C:31](O)=[O:32])[CH:28]([CH3:30])[CH3:29])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.ClCCl>[C:16]([NH:26][C@H:27]([C:31]([O:1][C@@H:2]([CH3:15])[C:3]([O:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=1)=[O:4])=[O:32])[CH:28]([CH3:30])[CH3:29])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 726987N-Carbobenzoxy-L-valineHCID 11095877HCID 11095877, compound

Product 1

HCID 53733618HCID 53733618, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxybenzyl (S)-(+)-2-hydroxypropionate (7.6 g, 36 mmole), N-CBZ-L-valine (10.05 g, 40 mmole) and DMAP (0.98 g, 8 mmole) in 150 ml dichloromethane was added a solution of DCC (8.3 g, 40 mmole) and the mixture was stirred overnight at room temperature. The mixture was cooled to about 5° C. and the urethane was filtered. The filtrate was evaporated and the product was isolated by silica gel column chromatography. Yield: 14.4 g=90%

Workup

  1. temperatureThe mixture was cooled to about 5° C.
  2. filtrationthe urethane was filtered
  3. customThe filtrate was evaporated
  4. customthe product was isolated by silica gel column chromatography

Sources & evidence

ORD record
ord-305a509630c049e1b60a23777bf2b192
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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