Dimethylformamide → HCID 70076866, compound

HRID 1378034Notes

Reaction equation

HRID 1378034 reaction equation
[C:1](N1C=CN=C1)([N:3]1C=CN=C1)=O.[C:13](NCC(O)=O)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[NH2:25]/[C:26](=[N:46]\[OH:47])/[C:27]1[N:28]=[CH:29][N:30]2[C:36]3[CH:37]=[CH:38][C:39]([F:42])=[C:40]([F:41])[C:35]=3[C:34](=[O:43])[N:33]3[CH2:44][CH2:45][C@H:32]3[C:31]=12.[CH3:48]N(C)C=O>>[C:13]([C:48]1[O:47][N:46]([CH2:1][NH2:3])[CH:26]([C:27]2[N:28]=[CH:29][N:30]3[C:36]4[CH:37]=[CH:38][C:39]([F:42])=[C:40]([F:41])[C:35]=4[C:34](=[O:43])[N:33]4[CH2:44][CH2:45][C@H:32]4[C:31]=23)[N:25]=1)([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 22876641HCID 22876641, compound

Product 1

HCID 70076866HCID 70076866, compoundYield 76%

Procedure

2.7 g (16.9 mmol) of 1,1'-carbonyldiimidazole were added to a solution of 4.5 g (14.1 mmol) of BOC-glycine in 30 ml of dimethylformamide and the mixture was stirred at 50° for 30 minutes. Subsequently, 4.5 g (14.1 mmol) of (E)- and/or (Z)-(S)-1-(aminohydroxylimino-methyl)-7,8-difluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one were added and the mixture was stirred at 90° for 16 hours. The brown solution obtained was evaporated in a high vacuum and the brown residue obtained was chromatographed (silica gel, methylene chloride/methanol 19:1). There were obtained 4.9 g (76%) of (S)-1-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-7,8-difluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one as a colourless foam, Rf=0.21 (silica gel, methylene chloride/methanol 19:1).

Workup

  1. stirringthe mixture was stirred at 90° for 16 hours
  2. customThe brown solution obtained
  3. customwas evaporated in a high vacuum
  4. customthe brown residue obtained
  5. customwas chromatographed (silica gel, methylene chloride/methanol 19:1)

Sources & evidence

ORD record
ord-79b47a5228504263adae1cf4c84754c8
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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