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

HRID 19177

반응식

HRID 19177 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-88643da42a2d4fc7b2df92278bd8a00b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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