Ethylmorpholine → HCID 12944618, compound

HRID 904944Notes

Reaction equation

HRID 904944 reaction equation
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([OH:8])=O)[CH:3]([CH3:5])[CH3:4].[NH2:16][C@H:17]([C:33]([O:35][CH3:36])=[O:34])[CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24].Cl.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.C(N1CCOCC1)C>C(Cl)Cl>[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([NH:16][C@H:17]([C:33]([O:35][CH3:36])=[O:34])[CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])=[O:8])[CH:3]([CH3:4])[CH3:5]

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 83693Boc-L-ValineHCID 1293537127894-50-4

Product 1

HCID 12944618HCID 12944618, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.35 g of Boc-Val-OH and 6.6 g of H-Lys(Z)-OMe.HCl are subjected to a condensation reaction with 4.4 g of DCC in 50 ml of CH2Cl2, with the addition of 2.7 g of HOBt and 2.6 ml of N-ethylmorpholine (NEM). After filtering the mixture, the solvent is removed by distillation. The residue is taken up in ethyl acetate, washed successively with 2 N acetic acid, 1 M sodium bicarbonate and water and dried over sodium sulfate and, after removing the ethyl acetate by distillation, is recrystallized from diisopropyl ether. Yield 3.5 g, melting point 100°-102°, elementary analysis (C, H and N) correct.

Workup

  1. filtrationAfter filtering the mixture
  2. customthe solvent is removed by distillation
  3. washwashed successively with 2 N acetic acid, 1 M sodium bicarbonate and water
  4. dry with materialdried over sodium sulfate
  5. customafter removing the ethyl acetate
  6. distillationby distillation
  7. customis recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-d0bcfb8d73aa4ccabac0454e816f4e3c
Source dataset
uspto-grants-1983_12
Patent number
US04420424

Reaction notes

Loading…