Ethylmorpholine → H-Glu-Ile-Phe-OBut

HRID 904958Notes

Reaction equation

HRID 904958 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:15](O)=[O:16])[CH2:3][CH2:4][C:5](=[O:14])[O:6]CC1C=CC=CC=1.[NH2:28][C@H:29]([C:34]([NH:36][C@H:37]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:35])[C@H:30]([CH2:32][CH3:33])[CH3:31].Cl.C1CCC(N=C=NC2CCCCC2)CC1.C(N1CCOCC1)C.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.CCOCC>[NH2:1][C@H:2]([C:15]([NH:28][C@H:29]([C:34]([NH:36][C@H:37]([C:45]([O:47][C:48]([CH3:49])([CH3:51])[CH3:50])=[O:46])[CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:35])[C@H:30]([CH2:32][CH3:33])[CH3:31])=[O:16])[CH2:3][CH2:4][C:5](=[O:6])[OH:14]

Participants

8

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 30498605-(Phenylmethyl) hydrogen N-((phenylmethoxy)carbonyl)-L-glutamateHCID 131713278H-Ile-Phe-OBut.HCl

Product 1

HCID 131713279H-Glu-Ile-Phe-OBut

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

1.85 g of Z-Glu(OBzl)-OH, 1.85 g of H-Ile-Phe-OBut.HCl and 1.1 g of DCC are reacted, analogously to Example 21 (C), in the presence of 0.65 ml of N-ethylmorpholine and 0.7 g of HOBt in dimethylformamide, the product is subjected to catalytic hydrogenation and 2.4 g of the compound insoluble in ether are isolated.

Workup

  1. customare isolated

Sources & evidence

ORD record
ord-597aed4c12ed45e69d1288c3177c0dc6
Source dataset
uspto-grants-1983_12
Patent number
US04420424

Reaction notes

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