Reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.C(OC([NH:42][C@H:43]([C:50]([OH:52])=O)[CH2:44][N:45]1[CH:49]=[CH:48][CH:47]=[N:46]1)=O)C1C=CC=CC=1.[NH2:53][C@@H:54]([CH2:62][CH:63]1[CH2:68][CH2:67][CH2:66][CH2:65][CH2:64]1)[C@@H:55]([OH:61])[C@H:56]([CH:58]1[CH2:60][CH2:59]1)[OH:57]>C(#N)C>[NH2:42][C@@H:43]([CH2:44][N:45]1[CH:49]=[CH:48][CH:47]=[N:46]1)[C:50]([NH:53][C@@H:54]([CH2:62][CH:63]1[CH2:68][CH2:67][CH2:66][CH2:65][CH2:64]1)[C@@H:55]([OH:61])[C@H:56]([CH:58]1[CH2:60][CH2:59]1)[OH:57])=[O:52]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
1.03 g (2.83 mmol) of HBTU and 0.39 ml (2.83 mmol) of triethylamine were added to a solution of 820 mg (2.83 mmol) of N-[(benzyloxy)carbonyl]-3-(pyrazol-1-yl)-L-alanine [J. Am. Chem. Soc. 107, 7105 (1985)]and 644 mg (2.83 mmol) of (1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediol in 28 ml of acetonitrile and the mixture was stirred at room temperature overnight. The crystals obtained after filtration were dissolved in 30 ml of ethanol and hydrogenated at 400 for two hours. Filtration over diatomaceous earth and evaporation under reduced pressure yielded 670 mg of (S)-α-amino-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-3-(pyrazol-1-yl)propionamide, MS: 365 (M+H)+, as a colourless foam.
Workup
- customThe crystals obtained
- filtrationafter filtration
- dissolutionwere dissolved in 30 ml of ethanol
- filtrationFiltration
- customover diatomaceous earth and evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-b34087caac06438a9d4b9820a61fbc61
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05393875
Linked notes
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