Dimethyl Sulfoxide → (2S,3S)-2-(tert-butoxycarbonylamino)-3-(5-cyano-2-nitrophenylamino)butanoic acid

HRID 1486082ノート

反応式

HRID 1486082 の反応式
[NH2:1][C@@H:2]([CH3:15])[C@H:3]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:4]([OH:6])=[O:5].CS(C)=O.F[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[N+:29]([O-:31])=[O:30])[C:24]#[N:25].C(=O)(O)[O-].[Na+]>C([O-])([O-])=O.[Na+].[Na+]>[C:11]([O:10][C:8]([NH:7][C@@H:3]([C@@H:2]([NH:1][C:21]1[CH:22]=[C:23]([C:24]#[N:25])[CH:26]=[CH:27][C:28]=1[N+:29]([O-:31])=[O:30])[CH3:15])[C:4]([OH:6])=[O:5])=[O:9])([CH3:14])([CH3:13])[CH3:12]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 516892Sodium Bicarbonate2 回HCID 27833993-Fluoro-4-nitrobenzonitrileHCID 90079392(2S,3S)-3-Amino-2-((tert-butoxycarbonyl)amino)butanoic acid

生成物 1

HCID 72712348(2S,3S)-2-(tert-butoxycarbonylamino)-3-(5-cyano-2-nitrophenylamino)butanoic acid収率 108.6%

試薬・触媒・溶媒 1

HCID 10340Sodium Carbonate溶媒

反応条件

温度
55 °C

実験手順

A mixture of (2S,3S)-3-amino-2-(tert-butoxycarbonylamino)butanoic acid (3.14 g, 14.4 mmol), dimethylsulfoxide (40 ml), 3-fluoro-4-nitrobenzonitrile (2.63 g, 15.8 mmol), and sodium bicarbonate (4.83 g, 57.5 mmol) was stirred at 55° C. for 3 h. Additional NaHCO3 (0.9 g) was added and the mixture was stirred at 60° C. for 1 hour, then cooled to RT, diluted with cold sat. Na2CO3, and washed with MTBE. The aqueous phase was carefully acidified to pH ˜4 with solid citric acid and extracted with EtOAc (three times). The combined organic layers were washed with H2O twice and brine, dried over Na2SO4, filtered, and concentrated to provide (2S,3S)-2-(tert-butoxycarbonylamino)-3-(5-cyano-2-nitrophenylamino)butanoic acid (5.7 g, quant.).

後処理

  1. stirringthe mixture was stirred at 60° C. for 1 hour
  2. temperaturecooled to RT
  3. washwashed with MTBE
  4. extractionextracted with EtOAc (three times)
  5. washThe combined organic layers were washed with H2O twice
  6. dry with materialbrine, dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-ce5bd089586e46c1aaff2df77e857bee
出典データセット
uspto-grants-2016_08
特許番号
US09422331B2

反応ノート

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