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

HRID 1486082노트

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HRID 1486082 반응식
[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]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 516892Sodium Bicarbonate2회HCID 27833993-Fluoro-4-nitrobenzonitrileHCID 90079392(2S,3S)-3-Amino-2-((tert-butoxycarbonyl)amino)butanoic acid

생성물 1

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

시약·촉매·용매 1

HCID 10340Sodium Carbonate용매

반응 조건

온도
55 °C

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-ce5bd089586e46c1aaff2df77e857bee
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422331B2

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