Dimethylformamide → HCID 70076785, compound

HRID 1378140Notes

Reaction equation

HRID 1378140 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.[O:25]=[C:26]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[N:30]2[CH:37]=[N:38][C:39]([C:40](=[N:42][OH:43])[NH2:41])=[C:29]2[C@@H:28]2[CH2:44][CH2:45][N:27]12.[CH3:46]N(C)C=O>>[C:1]([C:46]1[O:43][N:42]([CH2:13][NH2:15])[CH:40]([C:39]2[N:38]=[CH:37][N:30]3[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[C:26](=[O:25])[N:27]4[CH2:45][CH2:44][C@H:28]4[C:29]=23)[N:41]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 54277862HCID 54277862, compound

Product 1

HCID 70076785HCID 70076785, compoundYield 89%

Procedure

36.4 g (205 mmol) of BOC-glycine were dissolved in 300 ml of N,N-dimethylformamide and treated portionwise with 35.8 g (220 mmol) of 1,1'-carbonyldiimidazole. The solution was stirred at 50° for 30 minutes, 54.7 g (194 mmol) of (S)-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1- c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoxime were added thereto and the mixture was stirred at 90° overnight. After evaporating the solvent the residue was dissolved in methylene chloride and the solution was washed with water, dried over magnesium sulfate and concentrated. By chromatography of the residue on silica gel while eluting with ethyl acetate there were obtained 73 g (89%) of (S)-1-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one as a white foam, which was used in the next step without further purification.

Workup

  1. stirringthe mixture was stirred at 90° overnight
  2. customAfter evaporating the solvent the residue
  3. dissolutionwas dissolved in methylene chloride
  4. washthe solution was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. washBy chromatography of the residue on silica gel while eluting with ethyl acetate

Sources & evidence

ORD record
ord-901728231b74489ba94cb82b0d0651da
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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