Dimethylformamide → 4-(Cbz-amino)benzaldehyde
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[Li]CCCC.CN([CH:27]=[O:28])C>C1COCC1>[CH:27]([C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1)=[O:28]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Benzyl 4-bromophenylcarbamate (20 g, 65.3 mmol) was taken in anhydrous THF (440 mL) and cooled to −78° C. To this solution, n-BuLi (55 mL, 137.2 mmol) was added dropwise and stirred for 0.5 h at −78° C. To this mixture, DMF (7.6 mL) was added dropwise and the reaction was allowed to warm to room temperature over a period of 5 h. The reaction mixture was quenched with 1 N HCl and then concentrated to remove THF, followed by addition of water. The mixture was extracted with three portions of ethyl acetate. The combined organic phases were washed with H2O, brine, and dried (MgSO4) filtered and concentrated. Trituration with hexanes and then with 20% ethyl acetate in hexanes afforded the title compound as a yellow solid.
Workup
- temperatureto warm to room temperature over a period of 5 h
- customThe reaction mixture was quenched with 1 N HCl
- concentrationconcentrated
- customto remove THF
- additionfollowed by addition of water
- extractionThe mixture was extracted with three portions of ethyl acetate
- washThe combined organic phases were washed with H2O, brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-95b06fa033a346b28d1ab4212403a9f4
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07279494B2
Reaction notes
Loading…