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

HRID 595109Notes

Reaction equation

HRID 595109 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 14, 6.2 g) was dissolved in methanol (200 mL) and 1M aqueous sodium hydroxide solution (50 mL) was added. The reaction mixture was stirred at room temperature for 30 minutes then the methanol was removed in vacuo and the residue was diluted with a mixture of ethyl acetate and water and then acidified with acetic acid. The layers were separated and the organic phase 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 a mixture of ethyl acetate and water
  3. customThe layers were separated
  4. dry with materialthe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-896a3df6cffb46a49954d9c2cfedcfec
Source dataset
uspto-grants-2016_01
Patent number
US09242997B2

Reaction notes

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