Potassium → HCID 58563092, compound

HRID 1186145Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([C@:8]([NH:15][C:16](=[O:19])[CH2:17]Cl)([CH3:14])[CH2:9][C:10]([OH:13])([CH3:12])[CH3:11])[CH:7]=1.[K]>C1(C)C=CC=CC=1.O.Cl.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([C@:8]2([CH3:14])[CH2:9][C:10]([CH3:12])([CH3:11])[O:13][CH2:17][C:16](=[O:19])[NH:15]2)[CH:7]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of N-[(S)-1-(5-bromo-2-fluoro-phenyl)-3-hydroxy-1,3-dimethyl-butyl]-2-chloro-acetamide (intermediate A13A) (3.11 g, 8.5 mmol) in toluene (150 ml) at 23° C. was added dropwise a solution of potassium amylate (1.7 M in toluene; 25.0 ml, 42 mmol) within 10 min (slightly exotermic). The light brown solution was stirred at 23° C. for 2 h. Diluted with water, 1N HCl and brine and extracted twice with ethyl acetate. The organic layers were washed with sat. NaHCO3 solution and brine, dried over Na2SO4, filtered and evaporated to give a light brown oil, which was purified by silica gel column chromatography with n-heptane/ethyl acetate to give the title compound as an off-white solid (1.05 g, 37%). MS (ISP): m/z=330.0 [(M+H)+] and 332.0 [(M+2+H)+].

Workup

customwithin 10 min
extractionextracted twice with ethyl acetate
washThe organic layers were washed with sat. NaHCO3 solution and brine
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated
customto give a light brown oil, which
customwas purified by silica gel column chromatography with n-heptane/ethyl acetate

Sources & evidence

ORD record: ord-7eede8be3f5d4693a7941e32f8f1d802
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673894B2

Reaction notes

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