(S)-2-(1-Methyl-2,2,2-trifluoroethoxy)-5-methylsulfonylbenzoic acid → (3-Hydroxy-azetidin-1-yl)-[5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone

HRID 1711760Notes

Reaction equation

HRID 1711760 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:14][C@@H:15]([CH3:20])[C:16]([F:19])([F:18])[F:17])=[C:9]([CH:13]=1)[C:10]([OH:12])=O)(=[O:4])=[O:3].[N:21]1[CH2:24][CH:23]([OH:25])[CH:22]=1>>[OH:25][CH:23]1[CH2:24][N:21]([C:10]([C:9]2[CH:13]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=[CH:7][C:8]=2[O:14][C@@H:15]([CH3:20])[C:16]([F:19])([F:18])[F:17])=[O:12])[CH2:22]1

Participants

3

Reactant 2

HCID 58863351(S)-2-(1-Methyl-2,2,2-trifluoroethoxy)-5-methylsulfonylbenzoic acidHCID 68505089Azetin-3-ol

Product 1

HCID 58673077(3-Hydroxy-azetidin-1-yl)-[5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanoneYield 43%

Procedure

Prepared in analogy to Example 1 from 5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid (Example A2(c)) and azetin-3-ol. The crude material was purified by flash chromatography (ethyl acetate/n-heptane) to yield the title compound as a white crystalline solid (yield 43%). MS (m/e): 367.9 (M+H+, 100%).

Workup

  1. customThe crude material was purified by flash chromatography (ethyl acetate/n-heptane)

Sources & evidence

ORD record
ord-4dcfbb65fa944941a1cfcf8a2250c9a8
Source dataset
uspto-grants-2010_09
Patent number
US07790763B2

Reaction notes

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