Sodium Hydroxide → HCID 68423785, compound

HRID 1957970Notes

Reaction equation

HRID 1957970 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]=[C:6]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:5]=1.[OH-].[Na+]>O1CCOCC1>[C:18]([O:17][C:15]([NH:14][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]=1)[C:3]([OH:22])=[O:2])=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68423371HCID 68423371, compound

Product 1

HCID 68423785HCID 68423785, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-tert-butoxycarbonylamino-5-(methylsulfonyl)-benzoic acid methyl ester (8.45 g; 25.65 mmol) was suspended in 1,4-dioxane (75 ml) and 100 ml of NaOH 1N solution. The reaction mixture was stirred at room temperature overnight. Then, it was concentrated in vacuo. The crude was suspended in water and treated with citric acid until pH 4. Then ethyl acetate was added, the organic phase separated, dried with MgSO4 and concentrated in vacuo. 6.85 g (22 mmol; 84% yield) of 3-tert-butoxycarbonylamino-5-(methylsulfonyl)-benzoic acid were obtained.

Workup

  1. concentrationThen, it was concentrated in vacuo
  2. additiontreated with citric acid until pH 4
  3. additionThen ethyl acetate was added
  4. customthe organic phase separated
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0294a607a01e4e2fb78b833c7c6fafb1
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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