Triethylamine → Benzyl [(1S)-1-(aminocarbonyl)-2,2-dimethylpropyl]carbamate
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([OH:19])=O)[C:13]([CH3:16])([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].C([N:24](CC)CC)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[NH2:24][C:17]([C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of N-[(benzyloxy)carbonyl]-tert-leucine (prepared according to the procedure in the literature; Emily, M. S. et al. Tetrahedron 2001, 57, 5303-5320.; 3.7 g, 14 mmol) in DMF (80 mL) were added ammonium chloride (900 mg, 17 mmol), triethylamine (5.9 mL, 42 mmol), HOBt (2.8 g, 18 mmol) and EDAPC (3.1 g, 18 mmol) and stirred at rt. After 17 h, the reaction mixture was quenched by addition of saturated aqueous sodium bicarbonate (100 mL) and extracted with ethyl acetate (100 mL×3). The combined organic layers were washed with water (100 mL×3), brine (50 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (2/1-1/1) to afford 3.0 g (82%) of the title compound.
Workup
- customthe reaction mixture was quenched by addition of saturated aqueous sodium bicarbonate (100 mL)
- extractionextracted with ethyl acetate (100 mL×3)
- washThe combined organic layers were washed with water (100 mL×3), brine (50 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (2/1-1/1)
Sources & evidence
- ORD record
- ord-7f046eddf09c4a759d8ffd4cb6588823
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08138177B2
Reaction notes
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