Hydrogen Peroxide → HCID 67224897, compound

HRID 1944764

Reaction equation

[OH-:1].[Na+].OO.[C:5]([C:7]1([NH:27][C:28](=O)[CH3:29])[CH2:12][CH2:11][CH:10]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH3:25])=[C:19]([CH3:26])[CH:18]=2)(=[O:16])=[O:15])[CH2:9][CH2:8]1)#[N:6]>C(O)C.O>[CH2:24]([O:23][C:20]1[CH:21]=[CH:22][C:17]([S:14]([NH:13][CH:10]2[CH2:9][CH2:8][C:7]3([N:27]=[C:28]([CH3:29])[NH:6][C:5]3=[O:1])[CH2:12][CH2:11]2)(=[O:15])=[O:16])=[CH:18][C:19]=1[CH3:26])[CH3:25]

Participants

Conditions

Temperature: 80 °C

Procedure

5N Sodium hydroxide (320 ul, 1.59 mmol) followed by 50% aqueous hydrogen peroxide (157 ul, 2.55 mmol) were added to solution of N-(1-cyano-4-(4-ethoxy-3-methylphenylsulfonamido)cyclohexyl)acetamide (Intermediate 126, 242 mg, 0.638 mmol) in ethanol (6.4 ml). The reaction was heated to 80° C. for three hours. LCMS indicated approximately 3:1 product:starting material by co-injection. The reaction was diluted with water and extract with four volumes ethyl acetate. The combined organics were dried over sodium sulfate, filtered and concentrate to 226 mg crude. TLC (10% methanol in ethyl acetate): Rf starting material 0.66; major spot Rf=0.25. The crude was chromatographed on Biotage 12M eluting 0-100% ethyl acetate in (10% methanol in ethyl acetate) to give the product as an off-white solid (117 mg, 0.308 mmol). LCMS [M+H]=380.2.

Workup

extractionextract with four volumes ethyl acetate
dry with materialThe combined organics were dried over sodium sulfate
filtrationfiltered
concentrationconcentrate to 226 mg crude
customThe crude was chromatographed on Biotage 12M
washeluting 0-100% ethyl acetate in (10% methanol in ethyl acetate)

Sources & evidence

ORD record: ord-1e07e2d0db0a4902aa10cc40ff7066e6
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394858B2

Linked notes

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