Sodium Hydroxide → HCID 11774888, compound

HRID 1434960Notes

Reaction equation

HRID 1434960 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[S:11][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][CH:19]3[CH2:24][C:23]([CH3:26])([CH3:25])[NH:22][C:21]([CH3:28])([CH3:27])[CH2:20]3)[N:13]=2)=[CH:9][CH:8]=1.[O-]O.S(=O)(O)[O-:32].[Na+].[OH-].[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:1][S:2]([CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[S:11][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][CH:19]3[CH2:24][C:23]([CH3:26])([CH3:25])[NH:22][C:21]([CH3:28])([CH3:27])[CH2:20]3)[N:13]=2)=[CH:9][CH:8]=1)=[O:32]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 18500Perhydroxyl radicalHCID 11774436HCID 11774436, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 11774888HCID 11774888, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Compound of Step C (650 mg, 1.55 mmol) was dissolved in 5 ml TFA and 3 ml DCM. At room temperature 79 mg (2.3 mmol) hydroperoxide 30% were added. This mixture was stirred at room temperature for 2 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: 0.35 g (50%).

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-ebcff6c06e4f46e0be596a5c462ab50c
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

Loading…