Hydrogen Peroxide → HCID 89691265, compound

HRID 1504003Notes

Reaction equation

[C:1]([CH2:3][C@H:4]1[CH2:15][CH2:14][C:13]2[S:12][C:11]3[N:10]=[CH:9][N:8]=[C:7]([O:16][CH2:17][CH:18]4[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]4)[C:6]=3[C:5]1=2)#[N:2].[OH:31][Li].O.OO>CO.C(OCC)(=O)C>[NH:21]1[CH2:20][CH2:19][CH:18]([CH2:17][O:16][C:7]2[N:8]=[CH:9][N:10]=[C:11]3[C:6]=2[C:5]2[C@@H:4]([CH2:3][C:1]([NH2:2])=[O:31])[CH2:15][CH2:14][C:13]=2[S:12]3)[CH2:23][CH2:22]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl 4-([[(3R)-3-(cyanomethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]methyl)piperidine-1-carboxylate (290 mg, 0.68 mmol, 1.00 equiv) in methanol (20 mL) were added LiOH.H2O (114 mg, 2.71 mmol, 4.01 equiv). This was followed by the addition of H2O2 (30%) (114 mg, 4.00 equiv) dropwise with stirring at 0° C. The resulting solution was stirred for 4 h at room temperature. The resulting solution was diluted with 50 mL of ethyl acetate. The resulting mixture was washed with 3×20 mL of brine. The mixture was dried over sodium sulfate and concentrated under vacuum. This resulted in 220 mg (73%) of tert-butyl 4-([[(3R)-3-(carbamoylmethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]methyl)piperidine-1-carboxylate as a white solid.

Workup

stirringThe resulting solution was stirred for 4 h at room temperature
washThe resulting mixture was washed with 3×20 mL of brine
dry with materialThe mixture was dried over sodium sulfate
concentrationconcentrated under vacuum
customThis resulted in 220 mg (73%) of tert-butyl 4-([[(3R)-3-(carbamoylmethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]methyl)piperidine-1-carboxylate as a white solid

Sources & evidence

ORD record: ord-a8a6b1b64da4495b9350c0c21f88935a
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212190B2

Reaction notes

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