Carbon Dioxide → (S)-1-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one

HRID 1377995Notes

Reaction equation

HRID 1377995 reaction equation
[C:1](NCC(O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:13](N1C=CN=C1)([N:15]1C=CN=C1)=O.[C:25](=O)=O.[Cl:28][C:29]1[C:34]2[C:35](=[O:50])[N:36]3[CH2:49][CH2:48][CH2:47][C@H:37]3[C:38]3[N:39]([CH:40]=[N:41][C:42]=3[C:43](=[N:45][OH:46])[NH2:44])[C:33]=2[CH:32]=[CH:31][CH:30]=1>CN(C)C=O>[C:1]([C:25]1[O:46][N:45]([CH2:13][NH2:15])[CH:43]([C:42]2[N:41]=[CH:40][N:39]3[C:33]4[CH:32]=[CH:31][CH:30]=[C:29]([Cl:28])[C:34]=4[C:35](=[O:50])[N:36]4[CH2:49][CH2:48][CH2:47][C@H:37]4[C:38]=23)[N:44]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 682631,1'-CarbonyldiimidazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 53703069(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamidoxime

Product 1

HCID 70108885(S)-1-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-oneYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.16 g (23.6 mmol) of BOC-glycine were dissolved in 30 ml of N,N-dimethylformamide and treated portionwise with 4.08 g (25.2 mmol) of 1,1'-carbonyldiimidazole. After completion of the CO2 evolution the solution was stirred at 50° for 20 min. Then, 7.36 g (22.2 mmol) of (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamidoxime were added and the mixture was stirred at 90° overnight. The reaction mixture was evaporated, the residue was dissolved in methylene chloride and the solution was washed once with water and once with saturated sodium bicarbonate solution. After drying and concentrating there were obtained 7.75 g (74%) of (S)-1-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one, which was used in the next step without further purification.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washthe solution was washed once with water and once with saturated sodium bicarbonate solution
  4. customAfter drying
  5. concentrationconcentrating there

Sources & evidence

ORD record
ord-29b2512cfa6d4f9cb14e4890860d52ed
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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