Sodium Hydroxide → Methyl 3-bromo-6-bis-(tert-butoxycarbonyl)amino-2-hydroxybenzoate

HRID 715948Notes

Reaction equation

HRID 715948 reaction equation
[Br:1][C:2]1[C:3]([O:27]S(C2C=CC(C)=CC=2)(=O)=O)=[C:4]([C:9]([N:12]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[OH-].[Na+]>CO>[Br:1][C:2]1[C:3]([OH:27])=[C:4]([C:9]([N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:20]([O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86712111Methyl 3-bromo-6-bis-(tert-butoxycarbonyl)amino-2-(4-methylbenzenesulfonyloxy)benzoate2×

Product 1

HCID 70983234Methyl 3-bromo-6-bis-(tert-butoxycarbonyl)amino-2-hydroxybenzoateYield 97.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-bromo-6-bis-(tert-butoxycarbonyl)amino-2-(4-methylbenzenesulfonyl-oxy)benzoate (Intermediate 10, 6.2 g) was dissolved in methanol (200 mL) and 1M aqueous sodium hydroxide (50 mL) was added. The mixture was stirred at room temperature for 30 minutes. The methanol was removed in vacuo and the residue was diluted with ethyl acetate and water and acidified with acetic acid. The layers were separated and the organic layer was dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo to give methyl 3-bromo-6-bis-(tert-butoxycarbonyl)amino-2-hydroxybenzoate (4.51 g) as a sandy coloured solid.

Workup

  1. customThe methanol was removed in vacuo
  2. additionthe residue was diluted with ethyl acetate and water
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-444d7a441b714fc68a8ad4da558b324e
Source dataset
uspto-grants-2015_11
Patent number
US09187494B2

Reaction notes

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