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 1377995ノート

反応式

HRID 1377995 の反応式
[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]

参加物

6

反応物 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

生成物 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-one収率 74%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-29b2512cfa6d4f9cb14e4890860d52ed
出典データセット
uspto-grants-1997_09
特許番号
US05665718

反応ノート

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