Ethylmorpholine → Dicyclohexylcarbodiimide

HRID 1757733Notes

Reaction equation

HRID 1757733 reaction equation
N#N.N[C@H](C(N[C@@H](C[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C@H](O)C[C@@]1(C(N)=O)CCCN1C(C)(C)C)=O)CC(=O)N.C(OC(C1C=C2C(=CC=1)C=C(C(O)=O)C=C2)=O)C1C=CC=CC=1.O[C:59]1[C:67]2[N:66]=NN[C:63]=2[CH:62]=[CH:61][CH:60]=1.[CH2:68]([N:70]1CCOCC1)C>>[CH:67]1([N:66]=[C:68]=[N:70][CH:29]2[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]2)[CH2:63][CH2:62][CH2:61][CH2:60][CH2:59]1

Participants

5

Reactant 4

HCID 7525EthylmorpholineHCID 19031950HCID 19031950, compoundHCID 86748949HCID 86748949, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 10868Dicyclohexylcarbodiimide

Procedure

In a manner analogous to that described in Example from 295 mg of N2 -[3(S) [[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide, 204 mg of 6-(benzyloxycarbonyl ) -2-naphthoic acid, 20 mg of hydroxybenzotriazole, 77 mg of N-ethylmorpholine and 151 mgof dicyclohexylcarbodiimide there were obtained, after chromatography on silica gel using System G for the elution, 340 mg of N2 -[3(S)-[[N-[6-(benzyloxycarbonyl)-2-naphthoyl]-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide as an off-white solid from ethyl acetate/n-hexane: MS: m/e 736 [M+H]+.

Sources & evidence

ORD record
ord-c0a43f9595c34f8bbce7700641989664
Source dataset
uspto-grants-1995_08
Patent number
US05446161

Reaction notes

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