HCID 22858677, compound → HCID 22858678, compound

HRID 2396144Notes

Reaction equation

HRID 2396144 reaction equation
C([O:8][C:9](=[O:36])[C@H:10]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[NH:11][C:12]([N:14]([CH2:16][CH2:17][N:18]([C:20]([N:22]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:21])[CH3:19])[CH3:15])=[O:13])C1C=CC=CC=1.[H][H]>CO.[Pd]>[N:22]1([C:20]([N:18]([CH2:17][CH2:16][N:14]([CH3:15])[C:12]([NH:11][C@H:10]([C:9]([OH:36])=[O:8])[CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:13])[CH3:19])=[O:21])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 2

HCID 22858677HCID 22858677, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22858678HCID 22858678, compoundYield 107.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-[N-{2-[N-(hexahydro-1H-azepin-1-ylcarbonyl)-N-methylamino]ethyl}-N-methylaminocarbonyl]-L-phenylalanine benzyl ester (1.46 g) in methanol (20 ml) was hydrogenated over 10% palladium on carbon (146 mg) at 3 atmospheric pressure of hydrogen gas for 1 hour at ambient temperature. The solution was filtered and concentrated in vacuo to give N-[N-{2-[N-(hexahydro-1H-azepin-1-ylcarbonyl)-N-methylamino]ethyl}-N-methylaminocarbonyl]-L-phenylalanine (1.28 g) as an oil. Rf: 0.35 (chloroform:methanol:acetic acid, 16:1:1, V/V)

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2934d4d854f4a959f226f7e8093a3d4
Source dataset
uspto-grants-1996_02
Patent number
US05491132

Reaction notes

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