1,2-Dichloroethane → HCID 49853914, compound
Reaction equation
[C:1]12([C:7]3[CH:12]=[CH:11][C:10]([N:13]4[CH2:17][C@H:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15][C:14]4=[O:23])=[CH:9][CH:8]=3)[CH2:6][CH:5]1[CH2:4][NH:3][CH2:2]2.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[C:45](O)(=[O:48])[CH2:46][OH:47]>C(Cl)Cl>[OH:48][CH2:45][C:46]([N:3]1[CH2:4][CH:5]2[C:1]([C:7]3[CH:8]=[CH:9][C:10]([N:13]4[CH2:17][C@H:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15][C:14]4=[O:23])=[CH:11][CH:12]=3)([CH2:6]2)[CH2:2]1)=[O:47]Participants
Procedure
To a solution of hydrochloride salt of N-{3-[4-(3-aza-bicyclo[3.1.0]hex-1-yl)-phenyl]-2-oxo-oxazolidin-5(S)-yl-methyl}-acetamide (Intermediate IV) (300 mg, 0.72 mmol), in DCM (5 mL), were added EDC (180 mg, 0.94 mmol), HOBt (127 mg, 0.94 mmol) and NMM (0.32 mL, 2.89 mmol) and glycolic acid (60.4 mg, 0.79 mmol), at 0° C. The reaction mixture was stirred at r.t. and progress of the reaction was monitored by TLC. On completion, the reaction mixture was diluted with DCM (20 mL). The organic layer was washed with water (10 mL), brine (10 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 0.35:9.65 MeOH:CHCl3) to provide the title compound (160 mg, 59%) as off white solid.
Workup
- customat 0° C
- washThe organic layer was washed with water (10 mL), brine (10 mL)
- dry with materialdried over anhydrous sodium sulphate
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography (silica gel, 0.35:9.65 MeOH:CHCl3)
Sources & evidence
- ORD record
- ord-107afa38152042849860963592d3acc3
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906913B2
Reaction notes
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