Hydrogen Peroxide → HCID 86345243, compound

HRID 1504007Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:19][CH2:18][CH:17]([O:20][C:21]3[N:22]=[CH:23][N:24]=[C:25]4[C:32]=3[C:31]3[C@@H:30]([CH2:33][C:34]#[N:35])[CH2:29][CH2:28][C:27]=3[S:26]4)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[OH:36][Li].O.OO>CO>[N:11]1([CH:14]2[CH2:15][CH2:16][CH:17]([O:20][C:21]3[N:22]=[CH:23][N:24]=[C:25]4[C:32]=3[C:31]3[C@@H:30]([CH2:33][C:34]([NH2:35])=[O:36])[CH2:29][CH2:28][C:27]=3[S:26]4)[CH2:18][CH2:19]2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl-4-(4-[[(3R)-3-(cyanomethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yl]oxy]cyclohexyl)piperazine-1-carboxylate (260 mg, 0.52 mmol, 1.00 equiv) in methanol (15 mL) were added LiOH.H2O (150 mg, 3.57 mmol, 6.84 equiv), H2O2 (30%) (0.8 mL). The resulting solution was stirred for 4 h at 0° C. The reaction was then quenched by the addition of 10 mL of Na2SO3 (aq.). The resulting solution was extracted with 3×30 mL of dichloromethane and the organic layers combined and concentrated under vacuum. This resulted in 120 mg (45%) of tert-butyl 4-(4-[[(3R)-3-(carbamoylmethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yl]oxy]cyclohexyl)piperazine-1-carboxylate as a yellow oil.

Workup

customThe reaction was then quenched by the addition of 10 mL of Na2SO3 (aq.)
extractionThe resulting solution was extracted with 3×30 mL of dichloromethane
concentrationconcentrated under vacuum
customThis resulted in 120 mg (45%) of tert-butyl 4-(4-[[(3R)-3-(carbamoylmethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yl]oxy]cyclohexyl)piperazine-1-carboxylate as a yellow oil

Sources & evidence

ORD record: ord-a9d6db6f969a4d9f896548297fde7068
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212190B2

Reaction notes

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