Water → HCID 90098473, compound

HRID 81558Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C@:11]([NH:15][C:16](=[O:19])[CH2:17]Cl)(C)[CH2:12][OH:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[CH3:20]C([O-])(C)C.[K+].O>C(O)(C)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:11]2[NH:15][C:16](=[O:19])[CH2:17][O:13][C@@H:12]2[CH3:20])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

N—[(R)-1-(3-Bromo-5-nitro-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide (4.45 g, 10.76 mmol) and KOtBu (2.414 g, 21.52 g) were suspended in 55 ml tert-butanol under N2 and heated 100° C. for 30 min. After completion water was added to the reaction and tert-butanol was removed under reduced pressure. The product was extracted with ethyl acetate from the remaining aqueous phase. The organic phases were washed with water and brine, combined and dried over Na2SO4. Volatiles were removed under reduced pressure. The crude product was purified by automated column chromatography (cyclohexane/ethyl acetate) yielding the title compound as tan solid. 1H-NMR (360 MHz, DMSO-d6): 8.88 (1H, NH), 8.35 (s, 1H), 8.28 (s, 1H), 8.14 (s, 1H), 4.16 (m, 1H), 4.06 (s, 2H), 3.74 (m, 1H), 1.50 (s, 3H); MS: 316 [(M+H)+].

Workup

customwas removed under reduced pressure
extractionThe product was extracted with ethyl acetate from the remaining aqueous phase
washThe organic phases were washed with water and brine
dry with materialdried over Na2SO4
customVolatiles were removed under reduced pressure
customThe crude product was purified by automated column chromatography (cyclohexane/ethyl acetate)

Sources & evidence

ORD record: ord-58c474e3007043cb884247658de66598
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846658B2

Reaction notes

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