Sodium Hydroxide → HCID 70042193, compound

HRID 223330Notes

Reaction equation

HRID 223330 reaction equation
[CH3:1][S:2][C:3]1[C:8]2[C:9](=[O:27])[N:10]3[CH2:26][CH2:25][CH2:24][C@H:11]3[C:12]3[N:13]([CH:14]=[N:15][C:16]=3[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:36])C=1.[OH-:39].[Na+]>C(Cl)Cl>[CH3:1][S:2]([C:3]1[C:8]2[C:9](=[O:27])[N:10]3[CH2:26][CH2:25][CH2:24][C@H:11]3[C:12]3[N:13]([CH:14]=[N:15][C:16]=3[C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1)(=[O:36])=[O:39]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 53873707HCID 53873707, compound

Product 1

HCID 70042193HCID 70042193, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4 g (10.83 mmol) of t-butyl (S)-11,12,13,13a-tetrahydro-8-methylthio-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate are dissolved in 50 ml of methylene chloride and treated portionwise at room temperature with 4.0 g (about 20.8 mmol) of about 90 percent m-chloroperbenzoic acid. Subsequently, the mixture is warmed to boiling under reflux for 2.5 hours, then poured into 2 N sodium hydroxide and the methylene chloride solution is separated. The organic phase is dried over magnesium sulphate and evaporated. After recrystallization from chloroform/hexane, there is obtained t-butyl (S)-11,12,13,13a-tetrahydro-8-methylsulphonyl-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 244°.

Workup

  1. temperatureSubsequently, the mixture is warmed
  2. temperatureunder reflux for 2.5 hours
  3. customthe methylene chloride solution is separated
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. customevaporated
  6. customAfter recrystallization from chloroform/hexane

Sources & evidence

ORD record
ord-dcb2b07e8dc84ef5a7cf08554a2fc6ee
Source dataset
uspto-grants-1982_10
Patent number
US04353827

Reaction notes

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