Hydrochloric Acid → HCID 89455725, compound

HRID 1776533Notes

Reaction equation

HRID 1776533 reaction equation
[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:16]([O:18]C)=[O:17])[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1>[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:16]([OH:18])=[O:17])[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86679490HCID 86679490, compound

Product 1

HCID 89455725HCID 89455725, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxybenzoate (0.882 g, 2.454 mmol) in THF (15 ml), LiOH 1N (2.94 ml, 2.94 mmol) was added and the mixture was stirred at RT for 24 hours. The mixture was acidified with HCl 1N and extracted with EtOAc; the organic phase was washed with brine ad dried over Na2SO4. The solvent was removed and the residue was triturated with Et2O to afford after filtration 3-(N-(tert-butoxycarbonyl)-methylsulfonamido)-4-methoxybenzoic acid (0.487 g, 1.410 mmol, 57.5% yield, MS/ESI+ 367.9 [MNa]+).

Workup

  1. extractionextracted with EtOAc
  2. washthe organic phase was washed with brine ad
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed
  5. customthe residue was triturated with Et2O
  6. customto afford

Sources & evidence

ORD record
ord-562065757d674898a653d08d2a138fb9
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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