Hydrogen Peroxide → HCID 86695230, compound

HRID 1504069Notes

Reaction equation

[C:1]([CH2:3][CH2:4][C@H:5]1[C:17]2[C:16]3[C:15]([O:18][CH:19]4[CH2:24][CH2:23][CH:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:21][CH2:20]4)=[N:14][CH:13]=[N:12][C:11]=3[S:10][C:9]=2[CH2:8][CH2:7][CH2:6]1)#[N:2].[OH:33][Li].O.OO>CO>[C:1]([CH2:3][CH2:4][C@H:5]1[C:17]2[C:16]3[C:15]([O:18][CH:19]4[CH2:24][CH2:23][CH:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:31])[CH3:30])[CH2:21][CH2:20]4)=[N:14][CH:13]=[N:12][C:11]=3[S:10][C:9]=2[CH2:8][CH2:7][CH2:6]1)(=[O:33])[NH2:2]

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of tert-butyl N-(4-[[(13S)-13-(2-cyanoethyl)-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-3-yl]oxy]cyclohexyl)carbamate (300 mg, 0.66 mmol, 1.00 equiv) in methanol (15 mL) was added LiOH.H2O (82 mg, 1.95 mmol, 3.00 equiv) and H2O2 (30%, 0.5 mL) at 0° C. and the resulting solution was stirred for 2 h at 30° C. The reaction was quenched with saturated aqueous sodium sulfite, extracted with DCM (30 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (20:1) to give 240 mg (77%) of tert-butyl N-(4-[[(13S)-13-(2-carbamoylethyl)-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-3-yl]oxy]cyclohexyl)carbamate as a white solid.

Workup

customThe reaction was quenched with saturated aqueous sodium sulfite
extractionextracted with DCM (30 mL)
washwashed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-3d788d079e884d898c4eb16756871b23
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212190B2

Reaction notes

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