Hydrogen Peroxide → HCID 68115539, compound

HRID 1503945Notes

Reaction equation

HRID 1503945 reaction equation
[C:1]([CH:3]([O:33][CH3:34])[CH2:4][C@H:5]1[CH2:16][CH2:15][C:14]2[S:13][C:12]3[N:11]=[CH:10][N:9]=[C:8]([O:17][CH:18]4[CH2:23][CH2:22][CH:21]([N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20][CH2:19]4)[C:7]=3[C:6]1=2)#[N:2].[OH:35]O.[Li+].[OH-:38]>CO>[C:1]([C@@H:3]([O:33][CH3:34])[CH2:4][C@H:5]1[CH2:16][CH2:15][C:14]2[S:13][C:12]3[N:11]=[CH:10][N:9]=[C:8]([O:17][CH:18]4[CH2:23][CH2:22][CH:21]([N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:20][CH2:19]4)[C:7]=3[C:6]1=2)(=[O:35])[NH2:2].[C:1]([C@H:3]([O:33][CH3:34])[CH2:4][C@H:5]1[CH2:16][CH2:15][C:14]2[S:13][C:12]3[N:11]=[CH:10][N:9]=[C:8]([O:17][CH:18]4[CH2:19][CH2:20][CH:21]([N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:22][CH2:23]4)[C:7]=3[C:6]1=2)(=[O:38])[NH2:2]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 68110180HCID 68110180, compound

Product 2

HCID 68115539HCID 68115539, compoundHCID 86695119HCID 86695119, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tert-butyl N-(4-[[(3R)-3-(2-cyano-2-methoxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (360 mg, 0.74 mmol, 1.00 equiv) in methanol (10 mL) was added H2O2 (30%, 1 mL) and LiOH (36 mg, 1.50 mmol, 2.03 equiv) in a water/ice bath and the resulting mixture was stirred for 2 h. After completion, the reaction was quenched with saturated aqueous NaHSO3 and extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by preparative TLC (eluent with EtOAc/petroleum ether 1:1) to afford tert-butyl N-(4-[[(3R)-3-[(2S)-2-carbamoyl-2-methoxyethyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (100 mg) as a colorless oil and tert-butyl N-(4-[[(3R)-3-[(2R)-2-carbamoyl-2-methoxyethyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (140 mg) as a colorless oil, respectively. MS (ES): m/z 505 [M+H]+.

Workup

  1. customAfter completion, the reaction was quenched with saturated aqueous NaHSO3
  2. extractionextracted with 3×50 mL of ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by preparative TLC (eluent with EtOAc/petroleum ether 1:1)

Sources & evidence

ORD record
ord-95d6076761184bc0b7829614affe6ff5
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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