Borane;tetrahydrofuran → HCID 11348323, compound

HRID 2266892Notes

Reaction equation

B.C1COCC1.[Cl:7][C:8]1[S:12][C:11]([S:13]([NH:16][C@H:17]([C:24](O)=[O:25])[CH2:18][CH2:19][C:20]([F:23])([F:22])[F:21])(=[O:15])=[O:14])=[CH:10][CH:9]=1>C1COCC1>[Cl:7][C:8]1[S:12][C:11]([S:13]([NH:16][CH:17]([CH2:24][OH:25])[CH2:18][CH2:19][C:20]([F:21])([F:22])[F:23])(=[O:15])=[O:14])=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Borane-THF (1 M, 15 mL, 14.21 mmol) was added dropwise over 30 min at 0° C. to a solution of N-[(5-chlorothien-2-yl)sulfonyl]-5,5,5-trifluoronorvaline (1.0 g, 2.84 mmol) in THF (10 mL). The reaction was allowed to warm to 25° C. for 18 h and then was quenched by addition of 50 mL of 10% acetic acid in methanol. After solvent evaporation, the crude product was dissolved in EtOAc and washed with 1N HCl, H2O and saturated NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated to produce a crude oil (0.83 g) that was purified via flash chromatography, eluent: 1:6 ethyl acetate-hexane. This produced the title compound 5-chloro-N-[4,4,4-trifluoro-1-(hydroxymethyl)butyl]thiophene-2-sulfonamide as a colorless oil (0.46 g, 48%). Mass Spectrum (−ESI): 337 (M−H)−.

Workup

customwas quenched by addition of 50 mL of 10% acetic acid in methanol
customAfter solvent evaporation
dissolutionthe crude product was dissolved in EtOAc
washwashed with 1N HCl, H2O and saturated NaHCO3
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customto produce a crude oil (0.83 g) that
customwas purified via flash chromatography, eluent

Sources & evidence

ORD record: ord-77ee165e31034a61bdbb4433a3f199be
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858658B2

Reaction notes

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