Tetrahydrofuran → tert-butyl ((2S)-1-hydroxy-4-((1-methyl-1H-pyrazol-3-yl)amino)-4-oxobutan-2-yl)carbamate
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:17][C:18]([NH:20][C:21]1[CH:25]=[CH:24][N:23]([CH3:26])[N:22]=1)=[O:19])[C:10](OC(C)(C)C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[BH4-].[Li+].[Cl-].[NH4+]>CO>[OH:11][CH2:10][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:17][C:18]([NH:20][C:21]1[CH:25]=[CH:24][N:23]([CH3:26])[N:22]=1)=[O:19]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-4-((1-methyl-1H-pyrazol-3-yl)amino)-4-oxobutanoate (1.17 g) in a mixed solvent of THF (10.6 mL)/methanol (5.29 mL) was added lithium borohydride (0.484 g), and the mixture was stirred at room temperature for 2 hr, and then at 60° C. for 3 hr. The reaction mixture was poured into saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.553 g).
Workup
- waitat 60° C. for 3 hr
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-e75de6f46e074d7aa8e5f57e2d515d5a
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321757B2
Reaction notes
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