Benzyl-2-[2-(tert-butoxycarbonyl)-acetamido]acetate → 2-[2-(tert-Butoxycarbonyl)-acetamido]-acetic acid

HRID 1616999Notes

Reaction equation

HRID 1616999 reaction equation
C([O:8][C:9](=[O:22])[CH2:10][NH:11][C:12](=[O:21])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:17]([O:16][C:14]([CH2:13][C:12]([NH:11][CH2:10][C:9]([OH:22])=[O:8])=[O:21])=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 2

HCID 68088972Benzyl-2-[2-(tert-butoxycarbonyl)-acetamido]acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 866677562-[2-(tert-Butoxycarbonyl)-acetamido]-acetic acidYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl-2-[2-(tert-butoxycarbonyl)-acetamido]-acetate (14; 0.57 g, 1.85 mmol) was dissolved in methanol (15 mL), and then 10% Pd/C (0.06 g) was added therein with stirring for 1 h under pressure of 40 psi of hydrogen. After the reaction is completed, Pd/C was removed by filter paper and methanol was removed by concentration under reduced pressure to obtain colorless oil-like 15a (0.38 g; 100%). 1H-NMR (200 MHz) (DMSO) δ: 12.60 (br, s, 1H, CO2H), 8.07 (t, 1H, CONHCH2), 7.00 (t, 1H, NHBOC), 3.77 (d, 2H, CH2CO2H), 3.57 (d, 2H, CH2NHBOC), 1.40 [s, 9H, CO2C(CH3)3].

Workup

  1. customPd/C was removed
  2. filtrationby filter paper and methanol
  3. customwas removed by concentration under reduced pressure

Sources & evidence

ORD record
ord-1f9983e9802b4acca6eb9cfbd6eb35ac
Source dataset
uspto-grants-2014_07
Patent number
US08765934B2

Reaction notes

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