1,1'-Carbonyldiimidazole → (S)-N-methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:30][NH:31][O:32][CH3:33].CCN(C(C)C)C(C)C>C1COCC1.CN(C=O)C>[CH3:4][C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([N:31]([CH3:30])[O:32][CH3:33])=[O:16])[CH2:10][CH:11]([CH3:12])[CH3:13])=[O:7])([CH3:2])[CH3:3]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of N-(tert-butoxycarbonyl)-L-leucine (3.00 g, 13.0 mmol) in THF (25.0 mL) was added 1,1′-carbonyldiimidazole (2.52 g, 15.6 mmol) portionwise over about 10 min. After stirring 1 h at RT, a solution of N,O-dimethylhydroxylamine hydrochloride (1.39 g, 14.3 mmol) and DIPEA (2.49 mL, 14.3 mmol) in DMF (6.0 mL) was added. The reaction mixture was stirred for 2.5 h at RT, followed by concentration in vacuo. The residue was diluted with EtOAc (50 mL) and washed with 1 M aq. HCl (2×20 mL), saturated aq. NaHCO3 (2×20 mL), and brine (20 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to afford the title compound (2.34 g, 66%) as a clear, colorless oil. LC-MS m/z 275 (M+H)+, 1.17 min (ret time).
Workup
- stirringThe reaction mixture was stirred for 2.5 h at RT
- concentrationfollowed by concentration in vacuo
- additionThe residue was diluted with EtOAc (50 mL)
- washwashed with 1 M aq. HCl (2×20 mL), saturated aq. NaHCO3 (2×20 mL), and brine (20 mL)
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-ae0d9b2ede2b4493943663605d819d51
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841463B2
Reaction notes
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