Hydrogen Peroxide → HCID 86695133, compound

HRID 1503964Notes

Reaction equation

HRID 1503964 reaction equation
[Si:1]([O:8][CH:9]([CH2:12][C@H:13]1[CH2:24][CH2:23][C:22]2[S:21][C:20]3[N:19]=[CH:18][N:17]=[C:16]([O:25][CH:26]4[CH2:31][CH2:30][CH:29]([N:32]5[CH2:37][CH2:36][O:35][CH2:34][CH2:33]5)[CH2:28][CH2:27]4)[C:15]=3[C:14]1=2)[C:10]#[N:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:38][Li].O.OO>CO>[Si:1]([O:8][CH:9]([CH2:12][C@H:13]1[CH2:24][CH2:23][C:22]2[S:21][C:20]3[N:19]=[CH:18][N:17]=[C:16]([O:25][CH:26]4[CH2:27][CH2:28][CH:29]([N:32]5[CH2:33][CH2:34][O:35][CH2:36][CH2:37]5)[CH2:30][CH2:31]4)[C:15]=3[C:14]1=2)[C:10]([NH2:11])=[O:38])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 168937Lithium hydroxide, monohydrateHCID 86695131HCID 86695131, compound

Product 1

HCID 86695133HCID 86695133, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[(tert-butyldimethylsilyl)oxy]-3-[(3R)-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]propanenitrile (300 mg, 0.55 mmol, 1.00 equiv) in methanol (20 mL) was added LiOH.H2O (47 mg, 1.12 mmol, 3.55 equiv) and H2O2 (30%, 0.8 mL). The solution was stirred for 2 hr in a water/ice bath. After completion, the reaction was quenched by the addition of 30 mL of saturated aqueous Na2SO3 and extracted with 3×50 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, purification by column chromatography on silica gel with dichloromethane/methanol (20:1) afforded the 2-[(tert-butyldimethylsilyl)oxy]-3-[(3R)-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]propanamide (197 mg, 64%) as a colorless oil. MS (ES): m/z 561 [M+H]+.

Workup

  1. customAfter completion, the reaction was quenched by the addition of 30 mL of saturated aqueous Na2SO3
  2. extractionextracted with 3×50 mL of ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationAfter filtration and concentration
  5. customunder reduced pressure, purification by column chromatography on silica gel with dichloromethane/methanol (20:1)

Sources & evidence

ORD record
ord-ec841f922d7d4ae08c8c391386d82762
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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