Dicyclohexylcarbodiimide → HCID 23387487, compound

HRID 989993Notes

Reaction equation

HRID 989993 reaction equation
[C:1]([NH:20][C@H:21]([C:25]([OH:27])=[O:26])[CH:22]([CH3:24])[CH3:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([CH:31]([CH2:34]O)[CH2:32][OH:33])[CH:29]=[CH2:30].C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[C:1]([NH:20][C@H:21]([C:25]([O:27][CH2:34][CH:31]([CH2:28][CH:29]=[CH2:30])[CH2:32][OH:33])=[O:26])[CH:22]([CH3:23])[CH3:24])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 110623522-allyl-1,3-propandiolHCID 13918297HCID 13918297, compound

Product 1

HCID 23387487HCID 23387487, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-trityl-L-valine (5.5 g, 15.2 mmole), 2-allyl-1,3-propandiol (4.4 g, 38 mmol), N,N-dimethylamino pyridine (183 mg, 1.5 mmol) in dichloromethane (120 ml) was added DCC (3.5 g, 16.7 mmol). The reaction was kept under reflux overnight. After filtration through Celite, the organic phase was washed with sodium hydrogen carbonate aqueous solution and dried. Silica gel column chromatography gave 4.6 g intermediate 1-O—(N-trityl-L-valyl)-2-allyl-1,3-propandiol.

Workup

  1. temperatureunder reflux overnight
  2. filtrationAfter filtration through Celite
  3. washthe organic phase was washed with sodium hydrogen carbonate aqueous solution
  4. customdried

Sources & evidence

ORD record
ord-8556152dba3142558947db4efca35545
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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