7-Oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-sulfonyl chloride → HCID 69415009, compound

HRID 1351277Notes

Reaction equation

HRID 1351277 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 210986857-Oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-sulfonyl chlorideHCID 42182667HCID 42182667, compound

Product 1

HCID 69415009HCID 69415009, compound

Procedure

From 7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-sulfonyl chloride (the compound of Preparation Example 7) (286 mg) and (1R)-1-(4-fluorophenyl)-2-(methylamino)ethanol (the compound of Preparation Example 40) (212 mg), the title compound (356 mg) was obtained as a colorless 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 40) (212 mg)

Sources & evidence

ORD record
ord-a9f6a6b8299749c08d37ddd3583bc9f4
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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