Dimethylformamide → beta-[[[[4-Cyanophenyl]butyl]amino]carbonyl]aminobenzenepropanoic acid

반응식

[N-:1]=[C:2]=O.C(N([CH2:9][CH3:10])CC)C.[NH2:11][C@H:12]([CH2:19][C:20]([OH:22])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:23][N:24]([CH:26]=[O:27])C>>[C:2]([C:16]1[CH:17]=[CH:18][C:13]([CH2:12][CH2:9][CH2:10][CH2:23][NH:24][C:26]([NH:11][CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:19][C:20]([OH:22])=[O:21])=[O:27])=[CH:14][CH:15]=1)#[N:1]

참가 물질

반응물 4

HCID 6228Dimethylformamide

HCID 8471Triethylamine

HCID 105034Isocyanate

HCID 686703(3R)-3-amino-3-phenylpropanoic acid

생성물 1

HCID 54501418beta-[[[[4-Cyanophenyl]butyl]amino]carbonyl]aminobenzenepropanoic acid

반응 조건

온도: 23 °C

실험 절차

A solution of the isocyanate (6) (4.74 mmol), triethylamine (0.479 g, 4.74 mmol), β-phenylalanine (1.17 g, 7.11 mmol), and anhydrous DMF (10 mL) was warmed to 120° C. for 20 hours. After cooling to 23° C., the reaction mixture was concentrated on the rotovap, diluted with ethyl acetate (400 mL), washed with KHSO4 (1 N, 2×100mL), washed with brine (1×100 mL), and dried (Na2SO4). After concentration in vacuo. The urea was purified by flash chromatography (step gradient ethyl acetate with 1% acetic acid to ethyl acetate with 10% methanol and 1% acetic acid) to afford I.49 g (86%) of(7).