Diethyl 5-[[(phenylmethoxy)amino]carbonyl]-1,3-benzenedicarboxylate → HCID 12017545, compound

HRID 1352810Notes

Reaction equation

HRID 1352810 reaction equation
C1(C[O:8][NH:9][C:10]([C:12]2[CH:13]=[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:17]=2)=[O:11])C=CC=CC=1>C(O)C.[Pd]>[OH:8][NH:9][C:10]([C:12]1[CH:13]=[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:17]=1)=[O:11]

Participants

4

Reactant 1

HCID 12017544Diethyl 5-[[(phenylmethoxy)amino]carbonyl]-1,3-benzenedicarboxylate

Product 1

HCID 12017545HCID 12017545, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of diethyl 5-[[(phenylmethoxy)amino]carbonyl]-1,3-benzenedicarboxylate (0.742 g, 2.0 mmol) in ethanol (10 mL) was added a suspension of Pd/C in ethanol (5 mL), and the mixture was shaken under hydrogen (50 psi) for 20 hours. The catalyst was removed by filtration through a pad of celite and the filtrate was concentrated to give white powder. This material was washed with ethanol (10 mL×2) and dried under vacuum to give 0.380 g of white powder: 1H NMR (CD3OD) δ 1.44 (t, 6H), 4.45 (q, 4H), 8.60 (s, 2H), 8.72 (s, 1H). TLC: Rf 0.20 (EtOAc/Hexanes 1/1).

Workup

  1. customThe catalyst was removed by filtration through a pad of celite
  2. concentrationthe filtrate was concentrated
  3. customto give white powder
  4. washThis material was washed with ethanol (10 mL×2)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-c66ef028307a4a06adac39603aba888e
Source dataset
uspto-grants-2007_05
Patent number
US07220780B2

Reaction notes

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