Sodium Hydroxide → HCID 11282370, compound

HRID 1434961Notes

Reaction equation

HRID 1434961 reaction equation
[CH3:1][S:2]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[S:12][C:11]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH:20]3[CH2:25][C:24]([CH3:27])([CH3:26])[NH:23][C:22]([CH3:29])([CH3:28])[CH2:21]3)[N:14]=2)=[CH:10][CH:9]=1)=[O:3].[O-]O.S(=O)(O)[O-:33].[Na+].[OH-].[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:1][S:2]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[S:12][C:11]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH:20]3[CH2:25][C:24]([CH3:27])([CH3:26])[NH:23][C:22]([CH3:29])([CH3:28])[CH2:21]3)[N:14]=2)=[CH:10][CH:9]=1)(=[O:33])=[O:3]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 18500Perhydroxyl radicalHCID 11774888HCID 11774888, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 11282370HCID 11282370, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Compound of Step D (192 mg, 0.43 mmol) was dissolved in 5 ml TFA and 3 ml DCM. At room temperature 22 mg (0.64 mmol) hydroperoxide 30% were added. This mixture was stirred at room temperature for 4 hours. Afterwards 10 ml 10% sodium bisulfite solution was added and stirring continued for 15 minutes. The solution was basified with 40% NaOH and extracted with EtOAc. The crude was purified by chromatography on silicagel (DCM/MeOH/ammonia:9/1/0.1). Yield: 75 mg (37%).

Workup

  1. stirringstirring
  2. waitcontinued for 15 minutes
  3. extractionextracted with EtOAc
  4. customThe crude was purified by chromatography on silicagel (DCM/MeOH/ammonia:9/1/0.1)

Sources & evidence

ORD record
ord-740726f409304a0082847845c37acfea
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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