Ethylmorpholine → Dicyclohexylcarbodiimide

HRID 1757738Notes

Reaction equation

HRID 1757738 reaction equation
N#N.N[C@H](C(N[C@@H](CC1C=CC=CC=1)[C@H](O)C[C@@]1(C(N)=O)CCCN1C(C)(C)C)=O)CC(=O)N.C(O[C:43]([NH:45][C:46]1[C:47](C(O)=O)=[CH:48][C:49]2[C:54]([CH:55]=1)=CC=CC=2)=O)C1C=CC=CC=1.O[C:60]1[C:68]2N=N[NH:65][C:64]=2[CH:63]=[CH:62][CH:61]=1.C(N1CCOCC1)C>>[CH:64]1([N:65]=[C:43]=[N:45][CH:46]2[CH2:55][CH2:54][CH2:49][CH2:48][CH2:47]2)[CH2:68][CH2:60][CH2:61][CH2:62][CH2:63]1

Participants

5

Reactant 4

HCID 7525EthylmorpholineHCID 544637113-{[(Benzyloxy)carbonyl]amino}naphthalene-2-carboxylic acidHCID 86748949HCID 86748949, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 10868Dicyclohexylcarbodiimide

Procedure

In a manner analogous to that described in Example 27, from 295 mg of N2 -[3(S)-[[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide, 214 mg of 3-(benzyloxyformamido)-2-naphthoic acid, 90 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, 380 mg of N2 -[3(S)-[[N-[3-(benzyloxyformamido)-2-naphthoyl]-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide as a white solid from methanol: MS: m/e 751 [M+H]+.

Sources & evidence

ORD record
ord-cc380c5e5b9e491b97f7916f159f3ed5
Source dataset
uspto-grants-1995_08
Patent number
US05446161

Reaction notes

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