Benzyl Bromide → Benzyl 3-[(tert-Butoxycarbonyl)aminomethyl]-5-Methyl-Hexanoate
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:11][C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:11][C:12]([O:14][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Procedure
To a stirred suspension of (37) (1.24 g, 4.78 mmol) and Cs2CO3 (1.56 g, 4.78 mmol) in DMF (20 mL) was added benzyl bromide (0.56 mL, 4.68 mmol). The resulting mixture was stirred at ambient temperature until the reaction was complete (˜2 h, as monitored by LC/MS). The mixture was poured into ice water and extracted with dichloromethane. The combined organic phase was washed with water and brine, then dried over anhydrous Na2SO4. Filtration and removal of the solvent in vacuo afforded the title compound (38) (1.77 g, 100%), which was used without further purification in the following example. 1H—NMR (CDCl3, 400 MHz): δ 0.86 (2 d, 6H), 1.13 (m, 2H), 1.42 (s, 9H), 1.62 (m, 1H), 2.31 (m, 2H), 3.00 (m, 1H), 3.18 (m, 1H), 4.75 (br.s, 1H), 5.10 (s, 2H), 7.33 (m, 5H). MS (ESI) m/z 372.30 (M+Na+).
Workup
- custom(˜2 h, as monitored by LC/MS)
- extractionextracted with dichloromethane
- washThe combined organic phase was washed with water and brine
- dry with materialdried over anhydrous Na2SO4
- filtrationFiltration and removal of the solvent in vacuo
Sources & evidence
- ORD record
- ord-b1f0f2a1843343a381a9581bc56d6b9d
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07423169B2
Reaction notes
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