Potassium hydroxy sulfite → HCID 90067100, compound

HRID 920160Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:30])=[C:6]([C@@:8]2([CH3:29])[N:16]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=3[O:26][CH3:27])[C:15](=[O:28])[C:11]3([CH2:14][CH2:13][CH2:12]3)S[CH2:9]2)[CH:7]=1.O[O:32][S:33]([O-:35])=O.[K+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:30])=[C:6]([C@@:8]2([CH3:9])[N:16]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=3[O:26][CH3:27])[C:15](=[O:28])[C:11]3([CH2:14][CH2:13][CH2:12]3)[S:33](=[O:35])(=[O:32])[CH2:29]2)[CH:7]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of (R)-7-(5-bromo-2-fluorophenyl)-8-(2,4-dimethoxybenzyl)-7-methyl-5-thia-8-azaspiro[3.5]nonan-9-one (1.7 g, 3.44 mmol, Eq: 1.00) in methanol (50 ml) was added at 23° C. Oxone® (4.23 g, 6.88 mmol, Eq: 2.00). The reaction mixture was stirred at 23° C. for 24 hours. The reaction mixture was carefully quenched by addition of water at 0° C., 10 ml of a diluted NaHSO3 solution, sat. NaHCO3 solution and ethyl acetate were added. Vigorous stirring was continued for 10 min. The organic layer was separated and washed with water, then dried over Na2SO4, filtered and evaporated to give (R)-7-(5-bromo-2-fluoro-phenyl)-8-(2,4-dimethoxy-benzyl)-7-methyl-5,5-dioxo-5λ6-thia-8-aza-spiro[3.5]nonan-9-one (1.9 g, 3.25 mmol, 94.5% yield) as an off-white foam. MS (ISP): m/z=526.4 [M+H]+ and 528.3 [M+2+H]+.

Workup

customThe reaction mixture was carefully quenched by addition of water at 0° C.
addition10 ml of a diluted NaHSO3 solution, sat. NaHCO3 solution and ethyl acetate were added
stirringVigorous stirring
waitwas continued for 10 min
customThe organic layer was separated
washwashed with water
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-109c6a96a64b4948b31fcc8a7f4a133a
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273042B2

Reaction notes

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