Dicyclohexylcarbodiimide → Z-(L)-Val-(L)-Phe morpholin-4-ylamide

HRID 1654683Notes

Reaction equation

HRID 1654683 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[NH:16]([C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[C@H:17]([C:21]([OH:23])=O)[CH:18]([CH3:20])[CH3:19].[NH2:34][C@H:35]([C:43]([OH:45])=[O:44])[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[N:46]1([NH-:52])[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1>C(Cl)Cl>[NH:16]([C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[C@H:17]([C:21]([NH:34][C@H:35]([C:43]([OH:45])=[O:44])[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:23])[CH:18]([CH3:19])[CH3:20].[N:46]1([NH-:52])[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 726987N-Carbobenzoxy-L-valineHCID 131718980H-(L)-Phe morpholin-4-ylamide

Product 1

HCID 131718981Z-(L)-Val-(L)-Phe morpholin-4-ylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.75 g of DCC are added to a solution of 2.14 g of Z-(L)-Val-OH in 80 ml of absolute ice-cooled methylene chloride and after stirring for 20 minutes at that temperature a solution of 2 g of H-(L)-Phe-morpholin-4-ylamide is added dropwise thereto over a period of 15 minutes. The reaction mixture is stirred for a further 24 hours at room temperature and the urea that forms is filtered off. The filtrate is washed in succession with aqueous sodium hydrogen carbonate solution and brine and, after drying over sodium sulfate, concentrated. Stirring with ether and removal of the insoluble residue by filtration yields, after concentration, the title compound which is processed further without additional purification. TLC Rf (D )=0.7.

Workup

  1. additionis added dropwise
  2. filtrationthe urea that forms is filtered off
  3. washThe filtrate is washed in succession with aqueous sodium hydrogen carbonate solution and brine
  4. dry with materialafter drying over sodium sulfate
  5. concentrationconcentrated
  6. stirringStirring with ether and removal of the insoluble residue by filtration
  7. customyields
  8. concentrationafter concentration
  9. customthe title compound which is processed further without additional purification

Sources & evidence

ORD record
ord-c680caf509fe442e82cdad350b0f24e3
Source dataset
uspto-grants-1995_04
Patent number
US05409927

Reaction notes

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