Dicyclohexylcarbodiimide → HCID 70425201, compound

HRID 647019Notes

Reaction equation

HRID 647019 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][OH:25].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([CH:24]([OH:25])[C:23]1[CH:26]=[CH:27][CH:28]=[C:21]([NH2:20])[CH:22]=1)=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 802933-Aminobenzyl alcohol

Product 1

HCID 70425201HCID 70425201, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-t-butyloxycarbonylphenylalanine (1.00 g, 3.8 mmole) is dissolved in 4 ml of dichloromethane, in which is then suspended m-aminobenzyl alcohol. The cooled mixture is treated with 0.78 g (3.8 mmole) of dicyclohexylcarbodiimide for 12 to 24 hours. Dicyclohexylurea is removed by filtration, using an ethyl acetate wash. The filtrate is extracted three times with saturated aqueous potassium bisulfate, three times with aqueous potassium bicarbonate, and once with brine. The organic layer is dried over magnesium sulfate, filtered, and blown dry under flowing nitrogen. Column chromatography using silica gel and chloroform eluent produces, after removal of solvent, 1.19 g (3.2 mmole) of pure product. Structure assignment is supported by elemental analysis (C,H,N).

Workup

  1. customDicyclohexylurea is removed by filtration
  2. washwash
  3. extractionThe filtrate is extracted three times with saturated aqueous potassium bisulfate, three times with aqueous potassium bicarbonate
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. customblown dry under flowing nitrogen
  7. customproduces

Sources & evidence

ORD record
ord-46423b5edd1c4068a29e0704e690f161
Source dataset
uspto-grants-1983_10
Patent number
US04407746

Reaction notes

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