HCID 11164385, compound → HCID 11245950, compound

HRID 2266900Notes

Reaction equation

[C:1]([C@@H:4]([NH:12][S:13]([C:16]1[S:17][C:18]([Cl:21])=[CH:19][CH:20]=1)(=[O:15])=[O:14])[C@H:5]([CH3:11])[CH2:6][C:7]([F:10])([F:9])[F:8])(=[O:3])[CH3:2].[CH3:22][Mg]Br.CCOC(C)=O.CCCCCC>C1COCC1>[Cl:21][C:18]1[S:17][C:16]([S:13]([NH:12][C@H:4]([C:1]([OH:3])([CH3:22])[CH3:2])[C@H:5]([CH3:11])[CH2:6][C:7]([F:10])([F:9])[F:8])(=[O:15])=[O:14])=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of N-[(1S,2R)-1-acetyl-4,4,4-trifluoro-2-methylbutyl]-5-chlorothiophene-2-sulfonamide (prepared as in Example 17, 0.100 g, 0.275 mmol) in THF (5 mL) was stirred under nitrogen at 0° C. Methyl magnesium bromide (3.0 M in ethyl ether, 0.266 mL, 0.824 mmol,) was added dropwise and the resulting solution was stirred for 19 h at 25° C. After this time period, the reaction was complete by TLC (1:2 EtOAc/hexane). The solution was quenched with saturated aqueous NH4Cl (10 mL) and extracted with ether (40 mL). The organic layer was washed with brine (20 mL) and then dried over MgSO4 to obtain a crude oil (0.110 g). The crude product was purified by the Biotage Flash™ 40 chromatography system, eluent: 1:4 EtOAc-hexanes, to afford 5-chloro-N-[(1S,2R)-4,4,4-trifluoro-1-(1-hydroxy-1-methylethyl)-2-methylbutyl]thiophene-2-sulfonamide as a white solid (0.049 g, 46.6%). Mass Spectrum (−ESI): 378 (M−H)−.

Workup

customThe solution was quenched with saturated aqueous NH4Cl (10 mL)
extractionextracted with ether (40 mL)
washThe organic layer was washed with brine (20 mL)
dry with materialdried over MgSO4
customto obtain a crude oil (0.110 g)
customThe crude product was purified by the Biotage Flash™ 40 chromatography system, eluent

Sources & evidence

ORD record: ord-be7eb5331bc24869ba749c62520bff64
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858658B2

Reaction notes

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