Methanesulfonyl chloride → Methyl 2'-fluoro-2-(2-methyl-5-((methylsulfonyl)oxy)cyclopentyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662453Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH:20]1[CH:24]([CH3:25])[CH2:23][CH2:22][CH:21]1[OH:26].[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH:20]1[CH:21]([O:26][S:28]([CH3:27])(=[O:30])=[O:29])[CH2:22][CH2:23][CH:24]1[CH3:25]

Participants

Conditions

Temperature: 0 °C

Procedure

A 250 mL round bottom flask was charged with 66.56D (mixture of diastereomers) (0.61 g, 1.7 mmol), DCM (10 mL), and TEA (0.28 mL, 2.0 mmol) and cooled to 0° C. To the cold solution was added methanesulfonyl chloride (available from Aldrich) (0.16 mL, 2.0 mmol) dropwise. The cooling bath was removed, and the mixture was stirred for 1 hour at ambient temperature. The mixture was diluted with EtOAc, washed with water and brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel flash chromatography (0-40% EtOAc/hexane) to afford 66.56E (mixture of diastereomers) (0.69 g, 93% yield) as a colorless oil.

Workup

customThe cooling bath was removed
additionThe mixture was diluted with EtOAc
washwashed with water and brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe crude product was purified by silica gel flash chromatography (0-40% EtOAc/hexane)

Sources & evidence

ORD record: ord-1208b561eb10404da20843ead98d0adf
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Reaction notes

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