Water → HCID 53649012, compound

HRID 223341Notes

Reaction equation

HRID 223341 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[C:10]3[C@@H:9]3[CH2:22][CH2:23][CH2:24][N:8]3[C:7](=[O:25])[C:6]=2[CH:26]=1.[Br:27]N1C(=O)CCC1=O.O>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:16])=[C:10]3[C@@H:9]3[CH2:22][CH2:23][CH2:24][N:8]3[C:7](=[O:25])[C:6]=2[C:26]=1[Br:27]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 54484612HCID 54484612, compound

Product 1

HCID 53649012HCID 53649012, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.5 g (4.2 mmol) of t-butyl (S)-7-amino-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate and 0.783 g (4.4 mmol) of N-bromosuccinimide in 15 ml of dimethylformamide are stirred at room temperature for 45 minutes, subsequently poured into 250 ml of water and extracted three times with chloroform. The chloroform solution is washed three times with water, dried over magnesium sulphate and evaporated. The residue obtained is chromatographed on silica gel using chloroform containing 4% methanol for the elution. Recrystallization of the material obtained from ethyl acetate yields t-butyl (S)-7-amino-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 245°-246°.

Workup

  1. extractionextracted three times with chloroform
  2. washThe chloroform solution is washed three times with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue obtained
  6. customis chromatographed on silica gel
  7. washfor the elution
  8. customRecrystallization of the material
  9. customobtained from ethyl acetate

Sources & evidence

ORD record
ord-0a14010631904f2581fc8bee69ab4629
Source dataset
uspto-grants-1982_10
Patent number
US04353827

Reaction notes

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