Trifluoroacetic acid → 3-[2(R)-Hydroxypropyl]amino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]-butanamide

HRID 1033442Notes

Reaction equation

HRID 1033442 reaction equation
C([O:8][C@H:9]([CH3:31])[CH2:10][NH:11][C:12]([CH3:30])([CH3:29])[CH2:13][C:14]([NH:16][C@@H:17]1[CH2:23][CH2:22][C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[NH:19][C:18]1=[O:28])=[O:15])C1C=CC=CC=1.FC(F)(F)C(O)=O>CO.[Pd]>[OH:8][C@H:9]([CH3:31])[CH2:10][NH:11][C:12]([CH3:30])([CH3:29])[CH2:13][C:14]([NH:16][C@@H:17]1[CH2:23][CH2:22][C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[NH:19][C:18]1=[O:28])=[O:15]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 186514253-[2(R)-Benzyloxypropyl]amino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-benzazepin-3(R)-yl]butanamide

Product 1

HCID 186514293-[2(R)-Hydroxypropyl]amino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]-butanamideYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 23938PalladiumCatalyst

Procedure

A solution of 750 mg (1.40 mmol) of the intermediate obtained in Step A in methanol containing 2 drops of trifluoroacetic acid was hydrogenated at room temperature and 40 psi in the presence of 300 mg of 30% palladium on carbon for 3 days. The catalyst was removed by filtration through Celite and the filtrate concentrated under vacuum to give 600 mg (1.34 mmol, 96%) of product. 1H NMR (200 MHz, CD3OD): 1.22 (d,7 Hz,3H), 1.37 (s,3H), 1.39 (s,3H), 2.14 (m,1H), 2.3-3.0 (m,6H), 3.09 (dd;2,11 Hz;1H), 3.93 (m,1H), 4.38 (dd;8,12 Hz;1H), 7.05 (d,8 Hz,1H), 7.10-7.35 (m,3H).

Workup

  1. customwas hydrogenated at room temperature
  2. customThe catalyst was removed by filtration through Celite
  3. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-fe828718a93a4764bdc50bd2f8a04510
Source dataset
uspto-grants-1994_05
Patent number
US05310737

Reaction notes

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