Ethylmorpholine → N2 [3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1-phenyl-L-prolinamide

HRID 466840Notes

Reaction equation

HRID 466840 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.OC1C2N=[N:23][NH:22]C=2C=CC=1.C(N1CCOCC1)C.N#N.[NH2:36][C@@H:37]([CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C@H:38]([OH:54])[CH2:39][C@@:40]1([C:51]([NH2:53])=[O:52])[CH2:44][CH2:43][CH2:42][N:41]1[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.[CH2:62]([O:69][C:70]([NH:72][C@H:73]([C:78](O)=[O:79])[CH2:74][C:75](=[O:77])[NH2:76])=[O:71])[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1>O1CCCC1.C(OCC)(=O)C>[N:22]#[N:23].[CH2:62]([O:69][C:70]([NH:72][C@H:73]([C:78]([NH:36][C@@H:37]([CH2:55][C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1)[C@H:38]([OH:54])[CH2:39][C@@:40]1([C:51]([NH2:53])=[O:52])[CH2:44][CH2:43][CH2:42][N:41]1[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:79])[CH2:74][C:75](=[O:77])[NH2:76])=[O:71])[C:63]1[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=1

Participants

8

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 75314Benzyloxycarbonyl-asparagineHCID 86746222N2 [3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1-phenyl-L-prolinamideHCID 178418300HCID 178418300, compound

Product 1

HCID 86746220N2 [3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1-phenyl-L-prolinamideYield 42.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.208 g of dicyclohexylcarbodiimide, 0.124 g of hydroxybenzotriazole and 0.106 g of N-ethylmorpholine were added to a stirred solution of 0.315 g of N2 -[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1 -phenyl-L-prolinamide and 0.244 g of N-(benzyloxycarbonyl)-L-asparagine in 10 ml of tetrahydrofuran at 0° C. The mixture was stirred for 16 hours, then diluted with ethyl acetate and filtered. The filtrate was washed with sodium bicarbonate solution and sodium chloride solution and the solvent was then removed by evaporation. The residue was chromatographed on silica gel using dichloromethane/methanol (9:1) for the elution to give 0.22 g of N2 -[3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -phenyl-L-prolinamide in the form of a white solid of melting point 169°-171° C. (from methanol).

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with sodium bicarbonate solution and sodium chloride solution
  3. customthe solvent was then removed by evaporation
  4. customThe residue was chromatographed on silica gel
  5. washfor the elution

Sources & evidence

ORD record
ord-2cce90a8e3384b4bab910b14d11e5f70
Source dataset
uspto-grants-1992_10
Patent number
US05157041

Reaction notes

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