Methyl chloroformate → HCID 67980670, compound

HRID 1400030Notes

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(N(CC)CC)C.Cl[C:32]([O:34][CH3:35])=[O:33]>C(Cl)Cl>[C:20]([NH:19][CH2:18][C@@H:16]1[O:15][C:14](=[O:23])[N:13]([C:10]2[CH:9]=[CH:8][C:7]([C:1]34[CH2:6][CH:5]3[CH2:4][N:3]([C:32]([O:34][CH3:35])=[O:33])[CH2:2]4)=[CH:12][CH:11]=2)[CH2:17]1)(=[O:22])[CH3:21]

Participants

Conditions

Temperature: 0 °C

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) (200 mg, 0.57 mmol) in DCM (25 mL), was added triethyl amine (0.3 mL, 2.27 mmol). The resulting solution was cooled to 0° C. and methyl chloroformate (0.07 mL, 0.86 mmol) was added dropwise. 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 (100 mL). The organic layer was washed with water (25 mL), brine (25 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 0.2:9.8 MeOH:CHCl3) to provide the title compound (160 mg, 74%) as white solid.

Workup

washThe organic layer was washed with water (25 mL), brine (25 mL)
dry with materialdried over anhydrous sodium sulphate
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (silica gel, 0.2:9.8 MeOH:CHCl3)

Sources & evidence

ORD record: ord-905d2f4fbbf345a9999f2bce84049f0d
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906913B2

Reaction notes

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