Carbon Dioxide → HCID 22876606, compound

HRID 1378018Notes

Reaction equation

HRID 1378018 reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:13]([N:20]1C=CN=C1)([N:15]1C=CN=C1)=O.C(=O)=O.[F:28][C:29]([F:48])([F:47])[C:30]1[C:35]2[C:36](=[O:46])[N:37]3[CH2:45][CH2:44][C@H:38]3[C:39]3[N:40]([CH:41]=[N:42][CH:43]=3)[C:34]=2[CH:33]=[CH:32][CH:31]=1>CN(C)C=O>[C:1]([NH:8][CH2:9][C:10]1[O:12][N:20]=[C:13]([C:43]2[N:42]=[CH:41][N:40]3[C:34]4[CH:33]=[CH:32][CH:31]=[C:30]([C:29]([F:28])([F:47])[F:48])[C:35]=4[C:36](=[O:46])[N:37]4[CH2:45][CH2:44][C@H:38]4[C:39]=23)[N:15]=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 53950528HCID 53950528, compound

Product 1

HCID 22876606HCID 22876606, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.2 g (24 mmol) of BOC-glycine were dissolved in 40 ml of N,N-dimethylformamide and treated portionwise with 4.05 g (25 mmol) of 1,1'-carbonyldiimidazole. After completion of the CO2 evolution the solution was stirred at 50° for 20 min. Then, 7.7 g (22 mmol) of (S)-8-trifluoromethyl-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine were added and the mixture was stirred at 90° overnight. The reaction mixture was concentrated and the residue was dissolved in methylene chloride. By washing, drying and evaporating the organic phase there were obtained 7.82 g (72%) of (S)-1-[5-(N-BOC-aminomethyl)-1,2,4-oxadiazol-3-yl]-8-trifluoromethyl-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. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washBy washing
  4. customdrying
  5. customevaporating the organic phase there

Sources & evidence

ORD record
ord-8b0529345be8437bbca9d78e1e173085
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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