tert-Butyl N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-aminobenzoate → N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-aminobenzoic Acid

HRID 1830399Notes

Reaction equation

HRID 1830399 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:40])[C:5]([CH3:39])=[C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:35][C:36](=[O:38])[CH3:37])=[C:17]([CH:34]=2)[C:18]([NH:20][C:21]2[CH:33]=[CH:32][C:24]([C:25]([O:27]C(C)(C)C)=[O:26])=[CH:23][CH:22]=2)=[O:19])[C:7](=[O:11])[C:8]=1[O:9][CH3:10]>C(O)=O>[CH3:1][O:2][C:3]1[C:4](=[O:40])[C:5]([CH3:39])=[C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:35][C:36](=[O:38])[CH3:37])=[C:17]([CH:34]=2)[C:18]([NH:20][C:21]2[CH:33]=[CH:32][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=2)=[O:19])[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Participants

3

Reactant 1

HCID 22054238tert-Butyl N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-aminobenzoate

Product 1

HCID 22054291N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-aminobenzoic AcidYield 57.4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

tert-Butyl N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-aminobenzoate (0.250 g, 0.455 mmol) was dissolved in formic acid (3.0 ml) and the resulting solution was stirred at room temperature for 12 hours. The reaction solution was concentrated and the obtained residue was recrystallized from methanol to obtain the titled compound (0.129 g, 0.261 mmol, 57%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe obtained residue was recrystallized from methanol

Sources & evidence

ORD record
ord-062e2b27648641c39f716ffa44f47b90
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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