Acetic Acid → 3-[[1-(carboxy)-3-phenyl-propyl]amino]-1-t-butoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-benzazepin-2-one

온도

80 °C

Ethyl 3-benzoylacrylate (13a) (55.6 g, 272 mmoles) is dropped into a solution of (3S)-3-amino-1-t-butoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-benzazepin-2-one (11) (66.2 g, 228 mmoles) in 200 ml of toluene, at room temperature in 1 h. The resulting mixture is left under stirring for 18 h, then added with 10% Pd—C (26 g, 22 mmoles) and hydrogenated at 3 atm for 18 h at room temperature. After completion of the reaction the catalyst is filtered off through Celite, 50 ml of acetic acid are added and the solvent mixture is evaporated to kettle temperature of 110–120° C. The residue is taken up in 200 ml of toluene, 50 ml of acetic acid then cyclohexene (50 ml) and 10% Pd—C (26 g, 22 mmoles) are added. The reaction mixture is heated to 80° C. for 18 h, after that the catalyst is filtered off through Celite and solvents are evaporated off. The residue is taken up with isopropanol (500 ml) and the resulting precipitate is filtered, washed with 20 ml of isopropanol and dried to give 3-[[1-(carboxy)-3-phenyl-propyl]amino]-1-t-butoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-benzazepin-2-one (15) (60.7 g, yield: 54%).

1. waitThe resulting mixture is left
2. customAfter completion of the reaction the catalyst
3. filtrationis filtered off through Celite, 50 ml of acetic acid
4. additionare added
5. customthe solvent mixture is evaporated
6. customtemperature of 110–120° C
7. filtrationafter that the catalyst is filtered off through Celite and solvents
8. customare evaporated off
9. filtrationthe resulting precipitate is filtered
10. washwashed with 20 ml of isopropanol
11. customdried

ORD 기록

ord-2fe7a3fe31df42b3b2089adbb6e2ef75

출처 데이터셋

uspto-grants-2005_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06979736B2