(1S)-1-(4-fluorophenyl)-2-(methylamino)ethanol → N-[(2S)-2-(4-Fluorophenyl)-2-hydroxyethyl]-N-methyl-7-oxo-4,5,6,7-tetrahydro-1-benzothiophene-3-sulfonamide

HRID 1351276Notes

Reaction equation

HRID 1351276 reaction equation
[O:1]=[C:2]1[C:7]2[S:8][CH:9]=[C:10]([S:11](Cl)(=[O:13])=[O:12])[C:6]=2[CH2:5][CH2:4][CH2:3]1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([C@H:22]([OH:26])[CH2:23][NH:24][CH3:25])=[CH:18][CH:17]=1>>[F:15][C:16]1[CH:17]=[CH:18][C:19]([C@H:22]([OH:26])[CH2:23][N:24]([CH3:25])[S:11]([C:10]2[C:6]3[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[C:7]=3[S:8][CH:9]=2)(=[O:13])=[O:12])=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 15983834(1S)-1-(4-fluorophenyl)-2-(methylamino)ethanolHCID 210986857-Oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-sulfonyl chloride

Product 1

HCID 69415007N-[(2S)-2-(4-Fluorophenyl)-2-hydroxyethyl]-N-methyl-7-oxo-4,5,6,7-tetrahydro-1-benzothiophene-3-sulfonamide

Procedure

From 7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-sulfonyl chloride (the compound of Preparation Example 7) (285 mg) and (1S)-1-(4-fluorophenyl)-2-(methylamino)ethanol (the compound of Preparation Example 38) (230 mg), the title compound (370 mg) was obtained as a light brown solid, in the same way as Preparation Example 41. The NMR data matched the racemic mixture described in Preparation Example 48. The optical purity as measured by high performance liquid chromatography (ChiralPak AD-H, hexane:2-propanol=8:2) was >99% e.e.

Workup

  1. customthe compound of Preparation Example 38) (230 mg)

Sources & evidence

ORD record
ord-d8993b842cf944099491ab7fb5a21a48
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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