HCID 54045935, compound → HCID 13243524, compound

HRID 647862Notes

Reaction equation

HRID 647862 reaction equation
C(O[CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:8](=[O:22])[C@@H:7]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:6]1)(=O)C>C(O)C.[Pd]>[C:27]([O:26][C:24]([NH:23][C@H:7]1[CH2:6][CH2:5][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:8]1=[O:22])=[O:25])([CH3:30])([CH3:29])[CH3:28]

Participants

4

Reactant 1

HCID 54045935HCID 54045935, compound

Product 1

HCID 13243524HCID 13243524, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-acetoxy-3-(S)-t-butyloxycarbonylamino-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one (0.7 g) in ethanol (50 ml) was hydrogenated at 42 psi for 24 hours at 70° using 10% palladium on charcoal (0.5 g) as catalyst. The catalyst was filtered off and the solvent removed under reduced pressure to give 3-(S)-t-butyloxycarbonylamino-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one which, without further purification was converted to 3-(S)-amino-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one by the procedure described above; m.p. 99°-101°, [α]D =-297° (c=1 in ethanol).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-cd8ea3574b74423facf30a99076cafc9
Source dataset
uspto-grants-1983_10
Patent number
US04410520

Reaction notes

Loading…