HCID 57947370, compound → HCID 57947474, compound

HRID 341009Notes

Reaction equation

HRID 341009 reaction equation
C(O[C:9]([N:11](C)[C@H:12]([CH2:21][O:22][C:23](=[O:35])[NH:24][C:25]1[N:26]=[CH:27][C:28]2[C:33]([CH:34]=1)=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=O)C1C=CC=CC=1.[H][H]>[Pd].CO>[CH:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:34]=[C:25]([NH:24][C:23]([O:22][CH2:21][C@@H:12]([NH:11][CH3:9])[CH2:13][C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])=[O:35])[N:26]=1

Participants

5

Reactant 2

HCID 57947370HCID 57947370, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57947474HCID 57947474, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-tert-butyl 3-((benzyloxycarbonyl)(methyl)amino)-4-(isoquinolin-3-ylcarbamoyloxy)butanoate (1.8 g, 3.65 mmol) and MeOH (5 mL) was added 10% Pd—C (500 mg). The resulting mixture was stirred under 12 psi of hydrogen for 1 h. The mixture was filtered and concentrated, and the remaining residue was dried in vacuo to give (S)-tert-butyl 4-(isoquinolin-3-ylcarbamoyloxy)-3-(methylamino)butanoate (1.3 g), which was used without further purification. LRMS (M+H+) m/z 360.1

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customthe remaining residue was dried in vacuo

Sources & evidence

ORD record
ord-65bddd85dad846109c7f0fcc7e2cfe6b
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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