Dicyclohexylcarbodiimide → Z-D-Lys(Boc)-Phe-OMe

HRID 2309821Notes

Reaction equation

HRID 2309821 reaction equation
[NH:1]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C@@H:2]([C:15]([OH:17])=O)[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[NH2:28][C@H:29]([C:37]([O:39][CH3:40])=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.Cl.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C=O>[NH:1]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C@@H:2]([C:15]([NH:28][C@H:29]([C:37]([O:39][CH3:40])=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:17])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 7269420Z-D-Lys(Boc)-OH

Product 1

HCID 13753065Z-D-Lys(Boc)-Phe-OMe

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

43.2 g of Z-D-Lys(Boc)-OH, prepared analogously to the L-compound, are dissolved in 400 ml of dimethylformamide. 24.5 g of H-Phe-OMe.HCl, 15.33 g of HOBt, 14.53 ml of NEM and, with stirring, 25 g of DCC are added, and the mixture is left to stand overnight at room temperature. After the urea has been filtered off, the solvent is distilled off in vacuo and the oily residue is recrystallized from 200 ml of 80% strength ethanol.

Workup

  1. waitthe mixture is left
  2. filtrationAfter the urea has been filtered off
  3. distillationthe solvent is distilled off in vacuo
  4. customthe oily residue is recrystallized from 200 ml of 80% strength ethanol

Sources & evidence

ORD record
ord-fbdd41a5fb9d4a4380c00a21a4a5acc5
Source dataset
uspto-grants-1987_09
Patent number
US04696913

Reaction notes

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