Dicyclohexylcarbodiimide → N2 [3(S)-[N-(benzyloxycarbonyl)-L-asparaginylamino]-2(R)-hydroxy-4-phenylbutyl]-N1-tert.butyl-4(R)-hydroxy-L-prolinamide

HRID 54105Notes

Reaction equation

HRID 54105 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([OH:19])=O)[CH2:13][C:14](=[O:16])[NH2:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC1C2N=[N:27][NH:26]C=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.N#N.[NH2:47][C@@H:48]([CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C@H:49]([OH:64])[CH2:50][C@@:51]1([C:61]([NH2:63])=[O:62])[CH2:55][C@@H:54]([OH:56])[CH2:53][N:52]1[C:57]([CH3:60])([CH3:59])[CH3:58]>ClCCl.CO>[N:26]#[N:27].[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([NH:47][C@@H:48]([CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C@H:49]([OH:64])[CH2:50][C@@:51]1([C:61]([NH2:63])=[O:62])[CH2:55][C@@H:54]([OH:56])[CH2:53][N:52]1[C:57]([CH3:60])([CH3:58])[CH3:59])=[O:19])[CH2:13][C:14](=[O:16])[NH2:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 75314Benzyloxycarbonyl-asparagineHCID 86746268HCID 86746268, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 86746266N2 [3(S)-[N-(benzyloxycarbonyl)-L-asparaginylamino]-2(R)-hydroxy-4-phenylbutyl]-N1-tert.butyl-4(R)-hydroxy-L-prolinamideYield 37.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

In a manner analogous to that described in Example 92, from 0.133 g of N-(benzyloxycarbonyl)-L-asparagine, 0.068 g of hydroxybenzotriazole, 0.103 g of dicyclohexylcarbodiimide and 0.16 g of N2 -[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-4(R)-hydroxy-L-prolinamide, but using dichloromethane in place of ethyl acetate as the partitioning solvent and 20% methanol in dichloromethane for the chromatography and carrying out the re-evaporation with diethyl ether, there was obtained 0.1 g of N2 -[3(S)-[N-(benzyloxycarbonyl)-L-asparaginylamino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-4(R)-hydroxy-L-prolinamide of melting point 115° C.

Workup

  1. customthe re-evaporation with diethyl ether

Sources & evidence

ORD record
ord-82aaba92ec1840dfb9bb2275f24fa4dd
Source dataset
uspto-grants-1997_04
Patent number
US05620987

Reaction notes

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