Sodium Bicarbonate → HCID 59322198, compound

HRID 2060292Notes

Reaction equation

[C:1](=[O:4])([O-:3])O.[Na+].[CH2:6]([O:8][C:9]([C:11]1([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[CH2:15][CH2:14][NH:13][CH2:12]1)=[O:10])[CH3:7]>ClCCl>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:3][C:1]([N:13]1[CH2:14][CH2:15][C:11]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)=[CH:20][CH:19]=2)([C:9]([O:8][CH2:6][CH3:7])=[O:10])[CH2:12]1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydrogen carbonate (244 mg, 2.9 mmol) was added to a stirred solution of 3-(4′-fluoro-biphenyl-4-yloxymethyl)-pyrrolidine-3-carboxylic acid ethyl ester (see Preparation 65) (200 mg, 0.58 mmol) in dichloromethane (10 mL) and the resulting mixture cooled to 0° C. 2-Methoxy phenyl chloroformate (0.09 mL, 0.64 mmol) was added and the reaction mixture stirred at room temperature for 16 hours. The mixture was partitioned between water (25 mL) and dichloromethane (25 mL). The organic layer was separated, washed brine (25 mL), dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with 15% ethyl acetate in hexane to afford the title compound as a white solid (210 mg, 74%).

Workup

customThe mixture was partitioned between water (25 mL) and dichloromethane (25 mL)
customThe organic layer was separated
washwashed brine (25 mL)
dry with materialdried over magnesium sulphate
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel
washeluting with 15% ethyl acetate in hexane

Sources & evidence

ORD record: ord-5277c89c70aa4bbe9195d086030b561f
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278343B2

Reaction notes

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