HCID 10193197, compound → HCID 12111253, compound

HRID 640065Notes

Reaction equation

[CH3:1][Mg]Br.[Cl:4][C:5]1[S:9][C:8]([S:10]([NH:13][C@H:14]([CH:20]=[O:21])[CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])(=[O:12])=[O:11])=[CH:7][CH:6]=1>C1(C)C=CC=CC=1.C1COCC1.C1COCC1>[Cl:4][C:5]1[S:9][C:8]([S:10]([NH:13][C@H:14]([CH:20]([OH:21])[CH3:1])[CH:15]([CH2:16][CH3:17])[CH2:18][CH3:19])(=[O:12])=[O:11])=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of methylmagnesium bromide (1.4 M, 7.0 mL, 9.7 mmol) in toluene/THF (75:25) was added to a 0° C. solution of 5-chloro-N-[(S)-2-ethyl-1-formylbutyl]thiophene-2-sulfonamide (Example 221, 1.0 g, 3.2 mmol) in THF (30 mL). The mixture was warmed to 25° C. and after 2 h was quenched carefully with saturated aqueous ammonium chloride (25 mL). The mixture was extracted with EtOAc (3×25 mL). The organic extract was dried over Na2SO4, filtered and concentrated to give a colorless oil. The product was purified by column chromatography (Biotage), eluant: 1:4 EtOAc-hexane, to afford 5-chloro-N-[(S)-2-ethyl-1-(1-hydroxyethyl)butyl]thiophene-2-sulfonamide as a white solid (876 mg, 83%). The product is a diastereomeric mixture with a ratio of 3:7. mp 95-98° C. Anal. Calc'd for C12H20ClNO3S2: C, 44.23; H, 6.19; N, 4.30. Found: C, 44.25 H, 6.35; N, 4.29. Mass Spectrum (−ESI): 324 (M−H)−.

Workup

customwas quenched carefully with saturated aqueous ammonium chloride (25 mL)
extractionThe mixture was extracted with EtOAc (3×25 mL)
extractionThe organic extract
dry with materialwas dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customto give a colorless oil
customThe product was purified by column chromatography (Biotage), eluant

Sources & evidence

ORD record: ord-0ed534e775a040d1a1bfdbc4157b0a91
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691884B2

Reaction notes

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