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

HRID 489861
Notes
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Reaction equation

HRID 489861 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].C(O)(=O)C>C1(C)C=CC=CC=1.[Pd]>[C:11]([CH:10]([NH:16][CH: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]([CH3:34])([CH3:33])[CH3:35])=[O:30])[C:18]1=[O:36])[CH2:9][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([OH:13])=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 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 222629803-[[1-(carboxy)-3-phenyl-propyl]amino]-1-t-butoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-benzazepin-2-oneYield 56.7%

Reagents, catalysts & solvents 2

HCID 23938
Palladium
Catalyst
HCID 1140TolueneSolvent

Procedure

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, 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, 200 ml of acetic acid are added and the mixture is hydrogenated for a further 18 h, at 3 atm at room temperature, after that the catalyst is filtered off through Celite and the solvent mixture is evaporated to dryness. The residue is taken up with isopropanol (500 ml) and the resulting precipitate is filtered, washed with 20 ml of dichloromethane and dried to give 3-[[1-(carboxy)-3-phenyl-propyl]amino]-1-t-butoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-benzazepin-2-one (15) (58.5 g, yield: 52%).

Workup

  1. waitThe resulting mixture is left
  2. additionare added
  3. waitthe mixture is hydrogenated for a further 18 h, at 3 atm at room temperature
  4. filtrationafter that the catalyst is filtered off through Celite
  5. customthe solvent mixture is evaporated to dryness
  6. filtrationthe resulting precipitate is filtered
  7. washwashed with 20 ml of dichloromethane
  8. customdried

Sources & evidence

ORD record
ord-5212f677f7f54ae496d6c5f224bd927b
Source dataset
uspto-grants-2005_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06979736B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes