Thionyl Chloride → HCID 117759605, compound

HRID 1049594Notes

Reaction equation

[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=4[F:33])=[C:21]([CH:34](O)[C:35]4([CH3:40])[CH2:39][CH2:38][CH2:37][CH2:36]4)[CH:20]=3)[CH:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1.S(Cl)([Cl:44])=O>C1COCC1>[Cl:44][CH:34]([C:35]1([CH3:40])[CH2:39][CH2:38][CH2:37][CH2:36]1)[C:21]1[CH:20]=[C:19]([O:18][CH2:17][C:13]2[CH:12]=[C:11]([CH:4]([CH:1]3[CH2:3][CH2:2]3)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:16]=[CH:15][CH:14]=2)[CH:24]=[CH:23][C:22]=1[C:25]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=1[F:33]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 3-cyclopropyl-3-(3-(((2′-fluoro-2-(hydroxy(1-methylcyclopentyl)methyl)-5′-methoxybiphenyl-4-yl)oxy)methyl)phenyl)propanoate (99 mg) in THF (3 mL) was added thionyl chloride (64 μL) and the mixture was stirred at 50° C. for 15 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (95 mg) as a colorless oil.

Workup

customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-32b76397b7b640ccb8d07485605a8d3a
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382188B2

Reaction notes

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