Sodium Hydroxide → HCID 70040059, compound

HRID 223329Notes

Reaction equation

HRID 223329 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-].[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]

Participants

5

Reactant 3

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

Product 1

HCID 70040059HCID 70040059, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.0 g (10.38 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 25 ml of methylene chloride, treated portionwise at room temperature with 2.0 g (about 10.4 mmol) of about 90% percent m-chloroperbenzoic acid and left to stand at room temperature overnight. Then, the solution is poured into 2 N sodium hydroxide, the methylene chloride phase is separated, dried over magnesium sulphate and evaporated. After recrystallization from ethyl acetate/hexane, there is obtained t-butyl (S)-11,12,13,13a-tetrahydro-8-methylsulphinyl-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 224°-225° as a diastereoisomeric mixture.

Workup

  1. waitleft
  2. customthe methylene chloride phase is separated
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customAfter recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-5cbd725bb6fb40458a2f4f428ca156a9
Source dataset
uspto-grants-1982_10
Patent number
US04353827

Reaction notes

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