2-Methanesulfonylacetic acid → 1-(3-{4-[5-(3,4,5-Trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-furan-3-yl]-phenyl}-3-fluoro-azetidin-1-yl)-2-methanesulfonyl-ethanone

HRID 2277737Notes

Reaction equation

HRID 2277737 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:4]=[C:5]([C:10]2([C:26]([F:29])([F:28])[F:27])[O:14][CH:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4([F:25])[CH2:24][NH:23][CH2:22]4)=[CH:17][CH:16]=3)[CH2:11]2)[CH:6]=[C:7]([Cl:9])[CH:8]=1.[CH3:30][S:31]([CH2:34][C:35]([OH:37])=O)(=[O:33])=[O:32]>>[Cl:2][C:3]1[CH:4]=[C:5]([C:10]2([C:26]([F:27])([F:29])[F:28])[O:14][CH:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4([F:25])[CH2:22][N:23]([C:35](=[O:37])[CH2:34][S:31]([CH3:30])(=[O:33])=[O:32])[CH2:24]4)=[CH:17][CH:16]=3)[CH2:11]2)[CH:6]=[C:7]([Cl:9])[C:8]=1[Cl:1]

Participants

3

Reactant 2

HCID 37328412-Methanesulfonylacetic acidHCID 897253993-(4-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydrofuran-3-yl)phenyl)-3-fluoroazetidine hydrochloride

Product 1

HCID 716799771-(3-{4-[5-(3,4,5-Trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-furan-3-yl]-phenyl}-3-fluoro-azetidin-1-yl)-2-methanesulfonyl-ethanone

Procedure

Example 3 was prepared similarly to that of Example 1, except that Example 3, Intermediate 3 was reacted with methane sulfonyl acetic acid. Yield: 0.170 g (29.74%). 1H NMR (400 MHz, DMSO-d6) δ: 3.11 (s, 3H), 3.22 (d, J=17.24 Hz, 1H), 3.70 (d, J=17.16 Hz, 1H), 4.24 (s, 2H), 4.34 (d, J=21.64 Hz, 2H), 4.70 (d, J=21.6 Hz, 2H), 7.28 (d, J=8.12 Hz, 2H), 7.47 (d, J=8.24 Hz, 2H), 7.58 (s, 1H), 7.92 (s, 2H). LC-MS (m/z): =583.8 (M−H). HPLC purity: 99.64%.

Workup

  1. customExample 3 was prepared similarly to that of Example 1

Sources & evidence

ORD record
ord-a32ab5c7a4a44a21aed15bc5c382cda1
Source dataset
uspto-grants-2015_09
Patent number
US09133172B2

Reaction notes

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