Lithium Hydroxide → 2-{[(Tert-butoxycarbonyl)amino]sulfonyl}benzoic acid

HRID 1992122Notes

Reaction equation

HRID 1992122 reaction equation
[C:1]([O:5][C:6]([NH:8][S:9]([C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[C:14]([O:16]C)=[O:15])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>O1CCCC1.O>[C:1]([O:5][C:6]([NH:8][S:9]([C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[C:14]([OH:16])=[O:15])(=[O:10])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 14988086Methyl 2-{[(tert-butoxycarbonyl)amino]sulfonyl}benzoate

Product 1

HCID 587286752-{[(Tert-butoxycarbonyl)amino]sulfonyl}benzoic acidYield 51.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-{[(tert-butoxycarbonyl)amino]sulfonyl}benzoate 1a (400 mg, 1.3 mmol, 1 equiv) and lithium hydroxide (1.6 g, 39 mmol, 30 equiv) in tetrahydrofuran (10 mL) and water (2.5 mL) was stirred at RT for 18 h. The reaction was partially concentrated, acidified with 1N HCl and the product extracted into ethyl acetate. The organic layer was dried and concentrated to afford 2-{[(tert-butoxy carbonyl)amino]sulfonyl}benzoic acid (1b) as a white solid (200 mg, 51% yield). 1H NMR (300 MHz, DMSO) δ 7.94 (m, 1H), 7.71 (m, 3H), 1.26 (s, 9H). ES-LCMS m/z 300.08 (M−H).

Workup

  1. concentrationThe reaction was partially concentrated
  2. extractionthe product extracted into ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-af7d7a1d297641efb3d2d0716df423e4
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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