Trifluoroacetic acid → (S)-5-(Biphenyl-4-yl)-4-[(dimethylphosphonomethyl)-amino]-2-pentenoic acid ethyl ester

HRID 1078685ノート

反応式

HRID 1078685 の反応式
[CH2:1]([O:3][C:4](=[O:29])[CH:5]=[CH:6][C@@H:7]([NH:21]C(OC(C)(C)C)=O)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH3:2].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+].C(N(CC)C(C)C)(C)C.FC(S(O[CH2:59][P:60]([O:64][CH3:65])([O:62][CH3:63])=[O:61])(=O)=O)(F)F>C(Cl)Cl.O>[CH2:1]([O:3][C:4](=[O:29])[CH:5]=[CH:6][C@@H:7]([NH:21][CH2:59][P:60]([O:64][CH3:65])([O:62][CH3:63])=[O:61])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:13][CH:14]=1)[CH3:2]

参加物

8

反応物 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 22098913Dimethylphosphonomethyl trifluoromethylsulfonateHCID 54107369(S)-4-t-Butoxycarbonylamino-5-(biphenyl-4-yl)-pentenoic acid ethyl ester

生成物 1

HCID 53707898(S)-5-(Biphenyl-4-yl)-4-[(dimethylphosphonomethyl)-amino]-2-pentenoic acid ethyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒4 回

実験手順

(S)-4-t-Butoxycarbonylamino-5-(biphenyl-4-yl)-pentenoic acid ethyl ester (1.2 g, 3.03 mmol) is stirred for 1 hour in a 1/1 mixture of trifluoroacetic acid and methylene chloride (10 mL). A saturated aqueous solution of sodium bicarbonate (10 mL) is added and the product is extracted in methylene chloride (20 mL). The organic layer is dried over anhydrous sodium sulfate, filtered and cooled to 0° under nitrogen. To that solution is added N,N-diisopropylethylamine (0.633 mL, 3.63 mmol) in methylene chloride (2 mL), followed by a solution of dimethylphosphonomethyl trifiuoromethylsulfonate (Tetrahedron Lett., 1986, 1477; 907 mg, 3.33 mmol) in methylene chloride (2 mL). The mixture is stirred at room temperature for 18 hours. Water (20 mL) and methylene chloride (20 mL) are added. The organic layer is separated, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel, eluting with ethyl acetate to afford (S)-5-(biphenyl-4-yl)-4-[(dimethylphosphonomethyl)-amino]-2-pentenoic acid ethyl ester as a pale yellow oil (Rf=0.3 in EtOAc).

後処理

  1. extractionthe product is extracted in methylene chloride (20 mL)
  2. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. temperaturecooled to 0° under nitrogen
  5. customThe organic layer is separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by flash-chromatography on silica gel
  10. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-6de9a7a1e4fd4c70b64c47463485866f
出典データセット
uspto-grants-1996_08
特許番号
US05550119

反応ノート

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