Diisopropylethylamine → HCID 86730166, compound
Reaction equation
[NH2:1][C@@H:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4].Cl[C:9]1[N:14]=[C:13]([N:15]2[C@@H:19]([CH:20]([CH3:22])[CH3:21])[CH2:18][O:17][C:16]2=[O:23])[CH:12]=[CH:11][N:10]=1.CCN(C(C)C)C(C)C>O>[CH:20]([C@H:19]1[CH2:18][O:17][C:16](=[O:23])[N:15]1[C:13]1[CH:12]=[CH:11][N:10]=[C:9]([NH:1][C@@H:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4])[N:14]=1)([CH3:22])[CH3:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
To a solution of (S)-methyl 2-aminopropanoate (270 mg, 2.0 mmol, 1.2 equv. in 10 ml of DMSO) and (S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one (430 mg, 1.8 mmol, 1.0 equv.) was added DIPEA (805 mg, 6.23 mmol, 3.5 equiv), and the reaction mixture was heated at 110° C. for 120 min. The reaction mixture was poured into water (40 ml) and extracted with EtOAc (2×30 mL) and washed with water (30 mL). After separation, the aqueous phase was extracted with EtOAc (3×8 mL). Combined organics were dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (ethyl acetate in heptane 10 to 80%) to provide (S)-methyl 2-((4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-yl)amino)propanoate (260 mg, white solid) in 47.4% yield. LCMS m/z 309.1 (M+H)+ RT=1.53 min.
Workup
- extractionextracted with EtOAc (2×30 mL)
- washwashed with water (30 mL)
- customAfter separation
- extractionthe aqueous phase was extracted with EtOAc (3×8 mL)
- dry with materialCombined organics were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c7e5d4c780724138ac4ad0c29a3b7fd2
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957068B2
Reaction notes
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