Hydrogen Peroxide → Ammonium Hydroxide

HRID 1615855Notes

Reaction equation

HRID 1615855 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@:9]2([CH3:41])[N:18]([CH2:19][CH2:20][S:21][C:22]3[CH:23]=[C:24]4[C:37](=[CH:38][CH:39]=3)[CH2:36][C@:26]3([C:34]5[C:29](=[N:30][CH:31]=[CH:32][CH:33]=5)[NH:28][C:27]3=[O:35])[CH2:25]4)[C:17](=[O:40])[C:12]3([CH2:16][CH2:15][CH2:14][CH2:13]3)[NH:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[OH:42]O>CC(O)=O>[NH4+:11].[OH-:35].[F:1][C:2]1[CH:3]=[C:4]([C@@:9]2([CH3:41])[N:18]([CH2:19][CH2:20][S:21]([C:22]3[CH:23]=[C:24]4[C:37](=[CH:38][CH:39]=3)[CH2:36][C@:26]3([C:34]5[C:29](=[N:30][CH:31]=[CH:32][CH:33]=5)[NH:28][C:27]3=[O:35])[CH2:25]4)=[O:42])[C:17](=[O:40])[C:12]3([CH2:13][CH2:14][CH2:15][CH2:16]3)[NH:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 44468990HCID 44468990, compound

Product 2

HCID 14923Ammonium HydroxideHCID 44469123HCID 44469123, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of (2R)-5-({2-[(8R)-8-(3,5-difluorophenyl)-8-methyl-10-oxo-6,9-diazaspiro[4.5] dec-9-yl]ethyl}sulfanyl)-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (20.7 mg, 0.036 mmol, described in Example 20) in AcOH (0.50 mL) was added H2O2 (35% in H2O, 0.018 mL, 0.206 mmol). After 3 h, the reaction was quenched with saturated NaHCO3 solution (30 mL) and extracted with EtOAc (30 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified on silica gel, eluting with a gradient of CH2Cl2:CH3OH:NH4OH—100:0:0 to 90:10:0.1, to afford the title compound. MS: m/z=591 (M+1). HRMS: m/z=591.2243; calculated m/z=591.2236 for C32H33F2N4O3S.

Workup

  1. customthe reaction was quenched with saturated NaHCO3 solution (30 mL)
  2. extractionextracted with EtOAc (30 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified on silica gel
  7. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-2e9fa05290bf464eab2982463dc37bf6
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

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