Ammonium Chloride → 2-(Benzhydrylidene-amino)-3-(1-fluoro-cyclopentyl)-propionic acid ethyl ester

HRID 19177

反応式

HRID 19177 の反応式
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].CC(C)([O-])C.[K+].[F:27][C:28]1([CH2:33]OS(C(F)(F)F)(=O)=O)[CH2:32][CH2:31][CH2:30][CH2:29]1.[Cl-].[NH4+]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:33][C:28]1([F:27])[CH2:32][CH2:31][CH2:30][CH2:29]1)[CH3:2]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 23665647Potassium tert-butoxideHCID 86635233Trifluoro-methanesulfonic acid 1-fluoro-cyclopentylmethyl ester

生成物 1

HCID 866352342-(Benzhydrylidene-amino)-3-(1-fluoro-cyclopentyl)-propionic acid ethyl ester収率 58%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of N-(diphenylmethylene)glycine ethyl ester (1.94 g, 7.26 mmol) in N,N-dimethylformamide (10 mL) at 0° C. was added solid potassium t-butoxide (0.89 g, 7.93 mmol) over 10 min and the resulting solution stirred for an additional 15 min. A trifluoro-methanesulfonic acid 1-fluoro-cyclopentylmethyl ester (2 g, 7.99 mmol) solution in N,N-dimethylformamide (2 mL) was added and the resulting mixture allowed to warm to room temperature over 2 h. The resulting mixture was poured into saturated ammonium chloride and extracted with dichloromethane (200 mL). The organic phase was separated, washed with saturated sodium chloride solution and dried over magnesium sulfate. The mixture was filtered and evaporated and the residue purified by AnaLogix flash chromatography (AnaLogix SuperFlash Flash Column 120 g, 10% to 20% ethyl acetate/hexanes) which afforded 2-(benzhydrylidene-amino)-3-(1-fluoro-cyclopentyl)-propionic acid ethyl ester (1.36 g, 58%) as a yellow oil: 1H NMR (300 MHz, CDCl3) δ ppm 1.26 (t, J=7.1 Hz, 3H), 1.39-1.97 (m, 8H), 2.11-2.41 (m, 1H), 2.45-2.76 (m, 1H), 4.01-4.27 (m, 2H), 4.37 (dd, J=7.5, 4.5 Hz, 1H), 7.16-7.25 (m, 2H), 7.29-7.41 (m, 3H), 7.41-7.56 (m, 3H), 7.64 (d, J=7.8 Hz, 2H).

後処理

  1. extractionextracted with dichloromethane (200 mL)
  2. customThe organic phase was separated
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe mixture was filtered
  6. customevaporated
  7. customthe residue purified by AnaLogix flash chromatography (AnaLogix SuperFlash Flash Column 120 g, 10% to 20% ethyl acetate/hexanes) which

出典と根拠

ORDレコード
ord-88643da42a2d4fc7b2df92278bd8a00b
出典データセット
uspto-grants-2010_06
特許番号
US07741327B2

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