HCID 56993186, compound → HCID 57031516, compound

HRID 2396152Notes

Reaction equation

HRID 2396152 reaction equation
[N:1]1([C:8]([N:10]([CH2:12][CH2:13][N:14]([CH3:36])[C:15]([O:17][C@@H:18]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:19]([O:21]CC2C=CC=CC=2)=[O:20])=[O:16])[CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[N:1]1([C:8]([N:10]([CH2:12][CH2:13][N:14]([CH3:36])[C:15]([O:17][C@@H:18]([CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:19]([OH:21])=[O:20])=[O:16])[CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 56993186HCID 56993186, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57031516HCID 57031516, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl (2S)-2-[N-[2-{N-(hexahydro-1H-azepin-1-ylcarbonyl)-N-methylamino}ethyl]-N-methylaminocarbonyl]oxy-3-phenylpropionate (1.43 g) in methanol (20 ml) was hydrogenated over 10% palladium on carbon (0.2 g) at 3 atmospheric pressure of hydrogen gas for 1 hour at ambient temperature. The solution was filtered and concentrated in vacuo to give (2S)-2-[N-[2-{N-(hexahydro-1H-azepin-1-ylcarbonyl)-N-methylamino}ethyl]-N-methylaminocarbonyl]oxy-3-phenylpropionic acid (1.09 g) as an oil. Rf: 0.44 (chloroform:methanol:acetic acid, 16:1:1, V/V)

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa65792e60de4fc7aef7949287a2bbd7
Source dataset
uspto-grants-1996_02
Patent number
US05491132

Reaction notes

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