Ethylmorpholine → Benzyloxycarbonyl-asparagine

HRID 1757723Notes

Reaction equation

HRID 1757723 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[OH:16]C1C2N=NNC=2C=CC=1.C(N1CCOCC1)C.N#N.N[C@@H](CC1C=CC=CC=1)[C@H](O)C[C@@]1(C(N)=O)CCCN1CC1C=CC=CC=1.C(N1CCC[C@H]1C(NC[C@@H](O)[C@@H](N[C:86](=[O:103])[C@H:87]([CH2:99][C:100](=[O:102])[NH2:101])[NH:88][C:89]([O:91][CH2:92][C:93]1[CH:98]=[CH:97][CH:96]=[CH:95][CH:94]=1)=[O:90])CC1C=CC=CC=1)=O)C1C=CC=CC=1>>[CH2:92]([O:91][C:89]([NH:88][C@H:87]([C:86]([OH:103])=[O:16])[CH2:99][C:100](=[O:102])[NH2:101])=[O:90])[C:93]1[CH:94]=[CH:95][CH:96]=[CH:97][CH:98]=1

Participants

6

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 86746225HCID 86746225, compoundHCID 86746226HCID 86746226, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 75314Benzyloxycarbonyl-asparagine

Procedure

In a manner analogous to that described in Example 33, from 0.225 g of dicyclohexylcarbodiimide, 0.135 g of hydroxybenzotriazole, 0.115 g of N-ethylmorpholine, 0.38 g of N2 -[3(S)-amino-2(R)-hydroxy-4-Phenylbutyl]-N1 -benzyl-L-prolinamide and0.266 g of N-(benzyloxycarbonyl)-L-asparagine there was obtained 0.056 g ofN1 -benzyl-N2 -[3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl] amino]-2(R)-hydroxy-4-phenylbutyl]-L-prolinamide as a white solid: MS: m/e616 [M+H]+.

Sources & evidence

ORD record
ord-0e94583ccba6413f886672ad442f7d8a
Source dataset
uspto-grants-1995_08
Patent number
US05446161

Reaction notes

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