Dimethylamine → tert-Butyl (S)-(1-(dimethylamino)-1-oxo-3-phenylpropan-2-yl)carbamate
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N[C@@H](CCSSCC[C@H](N)C(O)=O)C(O)=O.N1(O[C:46](N(C)C)=[N+:47](C)[CH3:48])C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.CNC.O1CCCC1>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:10](=[O:11])[N:47]([CH3:48])[CH3:46])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a cooled solution of (S)-2-tert-butoxycarbonylamino-3-phenylpropionic acid (available from Aldrich; 5.3 g, 20 mmol) in dimethylformamide (50 mL) at 0° C. were added 1-hydroxybenzotriazole (available from 3B Scientific Corporation, Libertyville, Ill. 60048, USA; 2.97 g, 22 mmol) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluororophosphate (available from Aldrich; 8.30 g, 22 mmol). Diisopropylethylamine (10.7 mL, 61.4 mmol) and dimethylamine in tetrahydrofuran (2M, 15 mL, 30 mmol) were added dropwise. The mixture was stirred for 1 h at 0° C. and ethyl acetate was added. The mixture was washed with water and brine, and dried over sodium sulfate. Evaporation of the solvents gave ((S)-1-dimethylcarbamoyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester as a yellow oil (5.52 g) which was used in the next step without further purification.
Workup
- washThe mixture was washed with water and brine
- dry with materialdried over sodium sulfate
- customEvaporation of the solvents
Sources & evidence
- ORD record
- ord-40ac320e37f34faa881a62bcecb102fb
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08314250B2
Reaction notes
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