Carbon Dioxide → HCID 67713734, compound

HRID 1377992Notes

Reaction equation

HRID 1377992 reaction equation
[C:1](NCC(O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N1C=CN=C1)([N:15]1[CH:19]=[CH:18]N=C1)=O.C(=O)=O.[Cl:28][C:29]1[C:34]2[C:35](=[O:49])[N:36]3[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][C:30]=1[F:50]>CN(C)C=O>[C:1]([CH:19]([NH2:15])[C:18]1[O:46][N:45]=[C:43]([C:42]2[N:41]=[CH:40][N:39]3[C:33]4[CH:32]=[CH:31][C:30]([F:50])=[C:29]([Cl:28])[C:34]=4[C:35](=[O:49])[N:36]4[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 54002434(S)-8-chloro-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoxime

Product 1

HCID 67713734HCID 67713734, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

17.08 g (97 mmol) of BOC-glycine were dissolved in 165 ml of N,N-dimethylformamide and treated portionwise with 16.9 g (104 mmol) of 1,1'-carbonyldiimidazole. After completion of the CO2 evolution the solution was stirred at 50° for 30 min. Then, 30.8 g (91mmol) of (S)-8-chloro-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoxime were added and the mixture was stirred at 90° overnight. By evaporation of the solution and chromatography of the residue on 1.5 kg of silica gel while eluting with methylene chloride/methanol 19/1 there were obtained 36.8 g (84%) of (S)-1-[5-(BOC-aminomethyl)-1,2,4-oxadiazol-3-yl]-8-chloro-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, which was used in the next step without further purification.

Workup

  1. customBy evaporation of the solution and chromatography of the residue on 1.5 kg of silica gel
  2. washwhile eluting with methylene chloride/methanol 19/1 there

Sources & evidence

ORD record
ord-9d9289b82c064d149bd66398a1e0417f
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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