Ethyl Acetate → HCID 25418686, compound
Reaction equation
[C:1]([N:8]1CCNCC1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:14][CH2:15][N:16]([CH:20]([CH3:22])C)[CH:17]([CH3:19])C.[CH3:23]O.C(Cl)Cl.C[CH2:29][O:30][C:31](C)=[O:32]>CS(C)=O>[CH3:29][O:30][C:31](=[O:32])[C@H:22]([CH3:23])[CH2:20][N:16]1[CH2:15][CH2:14][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:19][CH2:17]1Participants
Conditions
- Temperature
- 62.5 °C
Procedure
To a stirred solution of 1-Boc-piperazine (1.00 g, 5.37 mmol) and DIPEA (2.81 ml, 16.11 mmol) in DMSO (20 ml) under nitrogen at rt was added methyl (S)-(−)-3-bromo-2-methyl propionate (1.03 ml, 8.05 mmol), and the reaction mixture was heated at 60-65° C. over weekend. More methyl (S)-(−)-3-bromo-2-methyl propionate (1.03 ml, 8.05 mmol) was added, and the reaction mixture was heated at 65° C. overnight. The reaction mixture was diluted with AcOEt, and successively washed with water, a saturated aqueous solution of sodium bicarbonate and brine. The aqueous layers were combined, extracted with ethyl acetate, and successively washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by Biotage (Snap 25 g cartridge: MeOH/DCM: 0/100 to 5/95 over 20 CV, then 05/95 to 10/90 over 5 CV), to afford the desired product 565 (523 mg, 1.83 mmol, 34% yield) as a yellow oil. MS (m/z): 231.13 and 287.27 (M+H).
Workup
- temperaturethe reaction mixture was heated at 65° C. overnight
- washsuccessively washed with water
- extractionextracted with ethyl acetate
- washsuccessively washed with water and brine
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by Biotage (Snap 25 g cartridge
Sources & evidence
- ORD record
- ord-f5d46c0f89944c8fb34e21be6e57f63a
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906852B2
Reaction notes
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