HCID 10215181, compound → GSI-136

HRID 640060Notes

Reaction equation

[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C@H:11]([C:17](O)=[O:18])[CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])(=[O:9])=[O:8])=[CH:4][CH:3]=1>C1COCC1>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C@H:11]([CH2:17][OH:18])[CH:12]([CH2:13][CH3:14])[CH2:15][CH3:16])(=[O:9])=[O:8])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To N-[(5-Chloro-2-thienyl)sulfonyl]-3-ethyl-L-norvaline (5.6 g, 17.2 mmol) in THF (150 mL) at 0° C. was added a solution of 1 M borane tetrahydrofuran complex in THF (69 mL, 69 mmol) dropwise via addition funnel. After 15 min, the reaction mixture was warmed to 25° C. and stirred for 18 h. It was then quenched with 90 mL of 10% AcOH in MeOH slowly. Volatiles were removed in vacuo. The residue was then dissolved in EtOAc (300 mL) and washed with sat. aqueous NaHCO3 (3×200 mL), dried (Na2SO4), and concentrated to a white precipitate (5.1 g, 96% yield, 96% chiral purity). The precipitate was recrystallized with heptane/EtOAc, 4:1, to give optically pure 5-chloro-N-[(S)-2-ethyl-1-(hydroxymethyl)butyl]-2-thiophenesulfonamide as white needles (4.4 g, 81% yield). [α]D25=+4.5° (c=1% SOLUTION, DMSO). Mass Spectrum (−ESI): 310 (M−H)−. Anal. Calc'd for C11H18ClNO3S2: C, 42.37; H, 5.82; N, 4.49. Found: C,42.37; H, 5.79; N, 4.38.

Workup

additiondropwise via addition funnel
customIt was then quenched with 90 mL of 10% AcOH in MeOH slowly
customVolatiles were removed in vacuo
dissolutionThe residue was then dissolved in EtOAc (300 mL)
washwashed with sat. aqueous NaHCO3 (3×200 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated to a white precipitate (5.1 g, 96% yield, 96% chiral purity)
customThe precipitate was recrystallized with heptane/EtOAc, 4:1

Sources & evidence

ORD record: ord-f5c6853e72664549b6b1c1dca9e63097
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691884B2

Reaction notes

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