Ethylmorpholine → HCID 178511789, compound

HRID 36840

Reaction equation

HRID 36840 reaction equation
C([O:8]C([NH:11][C@H:12]([C:19]([OH:21])=O)[CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1)=O)C1C=CC=CC=1.[NH:22]1[CH2:29][CH2:28]C[C@H:23]1[C:24]([NH2:26])=[O:25].[OH:30][C:31]1[C:39]2[N:38]=NN[C:35]=2[CH:34]=[CH:33]C=1.C(N1CC[O:45]CC1)C.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[O:8]=[C:23]1[NH:22][CH2:29][CH2:28][NH:26][C:24]1=[O:25].[NH2:11][C@H:12]([C:19]([N:38]1[CH2:33][CH2:34][CH2:35][C@H:39]1[C:31]([OH:30])=[O:45])=[O:21])[CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 111306L-ProlinamideHCID 178418300HCID 178418300, compoundHCID 178523877HCID 178523877, compound

Product 1

HCID 178511789HCID 178511789, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Synthetic L-histidyl-L-proline diketopiperazine was prepared by coupling benzyloxycarbonyl-L-histidine (about 20 mmol, ICN) with L-prolineamide (about 20 mmol, Vega-Fox) in the presence of hydroxybenzotriazole (about 40 mmol, Aldrich), N-ethylmorpholine (about 20 mmol, Aldrich) and dicyclohexylcarbodiimide (about 20 mmol, Pierce). The solution in about 175 ml of dimethylformamide was stirred in an ice-bath for about 3 hours and then overnight at room temperature.

Workup

  1. customovernight
  2. customat room temperature

Sources & evidence

ORD record
ord-d44bc0d5c7ec48bea947f870e3b66ef2
Source dataset
uspto-grants-1995_05
Patent number
US05418218

Linked notes

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