Benzyl 3-(2-hydroxybenzamido)butan-2-ylcarbamate → N-(3-aminobutan-2-yl)-2-hydroxybenzamide

HRID 85384Notes

Reaction equation

HRID 85384 reaction equation
[OH:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[C:4]([NH:6][CH:7]([CH3:21])[CH:8]([NH:10]C(=O)OCC1C=CC=CC=1)[CH3:9])=[O:5]>CO.[Pd]>[NH2:10][CH:8]([CH3:9])[CH:7]([NH:6][C:4](=[O:5])[C:3]1[CH:22]=[CH:23][CH:24]=[CH:25][C:2]=1[OH:1])[CH3:21]

Participants

4

Reactant 1

HCID 67174902Benzyl 3-(2-hydroxybenzamido)butan-2-ylcarbamate

Product 1

HCID 59193173N-(3-aminobutan-2-yl)-2-hydroxybenzamideYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 3-(2-hydroxybenzamido)butan-2-ylcarbamate (3.2 g, 9.36 mmol) and 10% Pd/C (0.32 g) in MeOH (120 mL) was stirred under a H2 (1 atm) atmosphere (RT, 16 h). The mixture was filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with MeOH-DCM (0-20%) to afford N-(3-aminobutan-2-yl)-2-hydroxybenzamide (1.67 g, 86%) as a yellow oil.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by column chromatography on silica gel
  4. washeluting with MeOH-DCM (0-20%)

Sources & evidence

ORD record
ord-7a015431fea64ddfb36fb4fc3eff33e0
Source dataset
uspto-grants-2014_09
Patent number
US08846972B2

Reaction notes

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