2-Butenoic acid, 4-oxo-4-phenyl-, ethyl ester → [2-Oxo-3-(2-oxo-5-phenyl-tetrahydro-furan-3-ylamino)-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl]-acetic acid tert-butyl ester

HRID 489866Notes

Reaction equation

HRID 489866 reaction equation
[C:1]([CH:9]=[CH:10][C:11]([O:13]CC)=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:16][C@H:17]1[CH2:23][CH2:22][C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[N:19]([CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:18]1=[O:36]>C1(C)C=CC=CC=1.[Pd]>[C:32]([O:31][C:29](=[O:30])[CH2:28][N:19]1[C:18](=[O:36])[CH:17]([NH:16][CH:10]2[CH2:9][CH:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[O:13][C:11]2=[O:12])[CH2:23][CH2:22][C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]1=2)([CH3:35])([CH3:33])[CH3:34]

Participants

5

Reactant 2

HCID 5698852-Butenoic acid, 4-oxo-4-phenyl-, ethyl esterHCID 63506241,1-Dimethylethyl ((3S)-3-amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)acetate

Product 1

HCID 85122760[2-Oxo-3-(2-oxo-5-phenyl-tetrahydro-furan-3-ylamino)-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl]-acetic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

Ethyl 3-benzoylacrylate (13a) (55.6 g, 250 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, 227 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, 50 ml of acetic acid are added and volatiles are distilled off at 110–120° C. inner temperature.

Workup

  1. waitThe resulting mixture is left
  2. customAfter completion of the reaction
  3. filtrationthe catalyst is filtered off
  4. addition50 ml of acetic acid are added
  5. distillationvolatiles are distilled off at 110–120° C. inner temperature

Sources & evidence

ORD record
ord-6edfd11df2a94b5aae59113372465169
Source dataset
uspto-grants-2005_12
Patent number
US06979736B2

Reaction notes

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