HCID 15520894, compound → HCID 15520895, compound

HRID 565138Notes

Reaction equation

HRID 565138 reaction equation
[C:1]([CH2:8][NH:9][C:10]1[C:11](=[CH:22][C:23]([O:26]CC2C=CC=CC=2)=[CH:24][CH:25]=1)[C:12]([O:14]CC1C=CC=CC=1)=[O:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H][H]>C1COCC1.C(OCC)(=O)C>[C:1]([CH2:8][NH:9][C:10]1[C:11](=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=1)[C:12]([OH:14])=[O:13])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 15520894HCID 15520894, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 15520895HCID 15520895, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

N-(Carbo-t-butoxymethyl)-5-benzyloxyanthranilic acid, benzyl ester (45.0 g, 101 mmol) was dissolved in 1:1 THF/ethyl acetate (1200 mL) in a 2 liter round bottom flask. The atmosphere was flushed with argon and 10% Pd/C (4.0 g) was added. The reaction atmosphere was replaced with hydrogen gas (4 purge-fill cycles) and the reaction mixture stirred under a balloon of hydrogen for 23 hours. The atmosphere was replaced with argon and the reaction mixture filtered through a pad of Celite, washing the Celite pad with methanol (250 mL). The solvents were removed in vacuo and the resulting yellow solid placed under high vacuum overnight to yield N-(carbo-t-butoxymethyl)-5-hydroxyanthranilic acid (27.1 g, 100% yield).

Workup

  1. customThe atmosphere was flushed with argon and 10% Pd/C (4.0 g)
  2. additionwas added
  3. customThe reaction atmosphere
  4. filtrationthe reaction mixture filtered through a pad of Celite
  5. washwashing the Celite pad with methanol (250 mL)
  6. customThe solvents were removed in vacuo
  7. customplaced under high vacuum overnight

Sources & evidence

ORD record
ord-957b1ff6481d480cba84254b22b4b03e
Source dataset
uspto-grants-2001_01
Patent number
US06171578B2

Reaction notes

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