Ethylmorpholine → H-Glu-Val-Val-OBut

HRID 904954Notes

Reaction equation

HRID 904954 reaction equation
[NH2:1][C@H:2]([C:6]([NH:8][C@H:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:7])[CH:3]([CH3:5])[CH3:4].Cl.[NH:21](C(OCC1C=CC=CC=1)=O)[C@H:22]([C:35](O)=[O:36])[CH2:23][CH2:24][C:25](=[O:34])[O:26]CC1C=CC=CC=1.C1C=CC2N(O)N=NC=2C=1.C(N1CCOCC1)C.C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C=O.CCOCC>[NH2:21][C@H:22]([C:35]([NH:1][C@H:2]([C:6]([NH:8][C@H:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:10]([CH3:11])[CH3:12])=[O:7])[CH:3]([CH3:5])[CH3:4])=[O:36])[CH2:23][CH2:24][C:25](=[O:26])[OH:34]

Participants

8

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 30498605-(Phenylmethyl) hydrogen N-((phenylmethoxy)carbonyl)-L-glutamateHCID 131713272H-Val-Val-OBut.HCl

Product 1

HCID 131713273H-Glu-Val-Val-OBut

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

31 g of H-Val-Val-OBut.HCl are subjected, analogously to Example 21 (B), to a condensation reaction with 37 g of Z-Glu(OBzl)-OH in dimethylformamide in the presence of 13.5 g of HOBt and 12.8 ml of N-ethylmorpholine, by means of 22 g of DCC. After working up analogously to this example, catalytic hydrogenation is carried out as described in Example 21 (C). The compound insoluble in ether is isolated and is a single substance according to thin layer chromatography. Yield 51 g.

Sources & evidence

ORD record
ord-fb0971d7b797436eb571404fb352eed0
Source dataset
uspto-grants-1983_12
Patent number
US04420424

Reaction notes

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