Dimethyl Sulfoxide → methyl [(2S)-1-(biphenyl-4-ylcarbonyl)-4-oxopyrrolidin-2-yl]acetate

HRID 225963Notes

Reaction equation

CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:16]=[CH:15][C:14]([C:17]([N:19]2[CH2:23][C@H:22]([OH:24])[CH2:21][C@H:20]2[CH2:25][C:26]([O:28][CH3:29])=[O:27])=[O:18])=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[C:11]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:12]=[CH:13][C:14]([C:17]([N:19]2[CH2:23][C:22](=[O:24])[CH2:21][C@H:20]2[CH2:25][C:26]([O:28][CH3:29])=[O:27])=[O:18])=[CH:15][CH:16]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of DMSO (31.4 μl, 0.44 mmol) in dichloromethane (1 ml) was added drop wise to a solution of oxalyl chloride (19 μl, 0.22 mmol) in dichloromethane (2 ml) at −78° C. under argon. After 15 min at −78° C., A solution of methyl [(2S,4R)-1-(biphenyl-4-ylcarbonyl)-4-hydroxypyrrolidin-2-yl]acetate (50 mg, 0.15 mmol) in dichloromethane (1 ml) was added drop wise. The reaction mixture was stirred at −78° C. for 1 hour and triethylamine (0.102 ml, 0.74 mmol) was added and allowed to warm to room temperature. The reaction mixture was diluted with ethyl acetate, washed with water then brine. The organic phase was dried (MgSO4) and concentrated to afford the methyl [(2S)-1-(biphenyl-4-ylcarbonyl)-4-oxopyrrolidin-2-yl]acetate (66 mg). Yield: 100%. HPLC purity: 99%

Workup

temperatureto warm to room temperature
washwashed with water
dry with materialThe organic phase was dried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-6dd253af78784f58a4b7a95384746900
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557136B2

Reaction notes

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