Thionyl Chloride → (S)-4-(5,5-Dimethyl-2-oxo-4-phenyloxazolidin-3-yl)benzoyl chloride

HRID 525327Notes

Reaction equation

[CH3:1][C:2]1([CH3:23])[O:6][C:5](=[O:7])[N:4]([C:8]2[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=2)[C@H:3]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.S(Cl)([Cl:26])=O>C(Cl)Cl>[CH3:1][C:2]1([CH3:23])[O:6][C:5](=[O:7])[N:4]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([Cl:26])=[O:13])=[CH:10][CH:9]=2)[C@H:3]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a vial charged with (S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)benzoic acid (0.200 g, 0.642 mmol) was added DCM (2.57 mL) followed by thionyl chloride (0.469 mL, 6.42 mmol). The vial containing the resulting mixture was sealed and shaken at 40° C. for 2 hours. LC-MS indicated near complete conversion to desired product (primarily methyl ester peak identified). The mixture was dried under reduced pressure providing the product as a light yellow solid. Mass of product not obtained. m/z (ESI) 326.2 (M+H)+ (methyl ester ionization observed).

Workup

additionThe vial containing the resulting mixture
customwas sealed

Sources & evidence

ORD record: ord-f88c0fab9ee44d0c8a44b8e053253174
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340549B2

Reaction notes

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