Dicyclohexylcarbodiimide → HCID 23387487, compound

HRID 489059Notes

Reaction equation

HRID 489059 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-a98254fe12de4980a6daa1618e70e966
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

Loading…