Benzyl 2-{3-[methoxy(methyl)carbamoyl]cyclobutylidene}acetate → 2-{3-[Methoxy(methyl)carbamoyl]cyclobutyl}acetic acid

HRID 2040658Notes

Reaction equation

HRID 2040658 reaction equation
[CH3:1][O:2][N:3]([CH3:21])[C:4]([CH:6]1[CH2:9][C:8](=[CH:10][C:11]([O:13]CC2C=CC=CC=2)=[O:12])[CH2:7]1)=[O:5]>[Pd].CCO>[CH3:1][O:2][N:3]([CH3:21])[C:4]([CH:6]1[CH2:9][CH:8]([CH2:10][C:11]([OH:13])=[O:12])[CH2:7]1)=[O:5]

Participants

4

Reactant 1

HCID 86666117Benzyl 2-{3-[methoxy(methyl)carbamoyl]cyclobutylidene}acetate

Product 1

HCID 598349352-{3-[Methoxy(methyl)carbamoyl]cyclobutyl}acetic acidYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on charcoal (10%, 0.1 g) was added to a solution of benzyl 2-{3-[methoxy(methyl)carbamoyl]cyclobutylidene}acetate (1.54 g, 5.32 mmol) in EtOH (20 ml) and stirred under an atmosphere of hydrogen at RT for 6 h. The reaction mixture was filtered through celite and evaporated to dryness to give a colorless oil (1.04 g, 89%); MS (ESI+) for C9H15NO4 m/z 202.00 [M+H]+; MS (ESI)− for C9H15NO4 m/z 200.05 [M−H]−; HPLC purity 92% (ret. time, 1.10 min); 1H NMR (500 MHz, MeOD) δH ppm 1.84-2.08 (2 H, m), 2.28-2.53 (4 H, m), 2.56-2.72 (1 H, m), 3.06-3.22 (3 H, m), 3.38-3.56 (1 H, m), 3.68 (3 H, d, J=8.04 Hz).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-379ba31e66bd4dacba242a6309092199
Source dataset
uspto-grants-2013_11
Patent number
US08580762B2

Reaction notes

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