Dicyclohexylcarbodiimide → HCID 23387487, compound

HRID 1790811Notes

Reaction equation

HRID 1790811 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-e16b8c466ff1470e810804f27a7337b6
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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