Dicyclohexylcarbodiimide → HCID 69941397, compound

HRID 324154Notes

Reaction equation

HRID 324154 reaction equation
[CH3:1][C@H:2]([C:11]([O:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)=[O:12])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH2:21]([O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[CH3:1][C@H:2]([C:11]([O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:33]([C:32]2[CH:36]=[CH:37][C:29]([O:28][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:30][CH:31]=2)=[O:34])=[CH:16][CH:15]=1)=[O:12])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 738804-(Benzyloxy)benzoic acidHCID 20645780HCID 20645780, compound

Product 1

HCID 69941397HCID 69941397, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{circle around (3)}: A mixture comprising 1.66 g of (S)-4-(1′-methylnonylcarbonyloxy)phenol, 1.37 g of 4-benzyloxybenzoic acid, 1.24 g of DCC and 10 g of dichloromethane was stirred at room temperature for 30 minutes. Then, a catalytic amount of 4-N,N-dimethylaminopyridine was added to the mixture, and the mixture was further stirred at room temperature for 12 hours. After finishing the reaction, insoluble substances were filtered off, followed by distilling off dichloromethane from the filtrate under reduced pressure. The resultant residue was purified by means of silica gel column chromatography, whereby 2.0 g of (S)-4-[4′-(1″-methylnonylcarbonyloxy)phenyloxycarbonyl]-1-benzyloxybenzene was obtained in the form of a colorless crystal.

Workup

  1. stirringthe mixture was further stirred at room temperature for 12 hours
  2. customthe reaction, insoluble substances
  3. filtrationwere filtered off
  4. distillationby distilling off dichloromethane from the filtrate under reduced pressure
  5. customThe resultant residue was purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-f1c78c18e21047358824379b5d8ec131
Source dataset
uspto-grants-2001_04
Patent number
US06217793B1

Reaction notes

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