1-(3-Fluoro-4-hydroxyphenyl)ethan-1-one → Rac-1-{3-fluoro-4-[1-(2-isopropoxy-5-methanesulfonyl-benzoyl)-pyrrolidin-3-yloxy]-phenyl}-ethanone

HRID 1711748Notes

Reaction equation

HRID 1711748 reaction equation
[CH:1]([O:4][C:5]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][C:6]=1[C:7]([N:9]1[CH2:13][CH2:12][CH:11]([O:14]S(C)(=O)=O)[CH2:10]1)=[O:8])([CH3:3])[CH3:2].[CH3:27][C:28]([C:30]1[CH:35]=[CH:34][C:33](O)=[C:32]([F:37])[CH:31]=1)=[O:29]>>[F:37][C:32]1[CH:31]=[C:30]([C:28](=[O:29])[CH3:27])[CH:35]=[CH:34][C:33]=1[O:14][CH:11]1[CH2:12][CH2:13][N:9]([C:7](=[O:8])[C:6]2[CH:19]=[C:20]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:21]=[CH:22][C:5]=2[O:4][CH:1]([CH3:3])[CH3:2])[CH2:10]1

Participants

3

Reactant 2

HCID 27373251-(3-Fluoro-4-hydroxyphenyl)ethan-1-oneHCID 58673069Rac-Methanesulfonic acid 1-(2-isopropoxy-5-methanesulfonyl-benzoyl)-pyrrolidin-3-yl ester

Product 1

HCID 58673061Rac-1-{3-fluoro-4-[1-(2-isopropoxy-5-methanesulfonyl-benzoyl)-pyrrolidin-3-yloxy]-phenyl}-ethanoneYield 62%

Procedure

Prepared in analogy to Example 3(c) from rac-methanesulfonic acid 1-(2-isopropoxy-5-methanesulfonyl-benzoyl)-pyrrolidin-3-yl ester (Example 14(a)) and 3-fluoro-4-hydroxyacetophenone. The crude material was purified by reversed phase HPLC (acetonitrile/water) to yield the title compound as an amorphous white solid (yield 62%). MS (m/e): 464.0 (M+H+, 100%).

Workup

  1. customThe crude material was purified by reversed phase HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-68227ac8b3b748aeb26913fc83c65243
Source dataset
uspto-grants-2010_09
Patent number
US07790763B2

Reaction notes

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