Lithium Hydroxide → HCID 89455725, compound

HRID 1776600Notes

Reaction equation

HRID 1776600 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-]>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

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 86679490HCID 86679490, compound

Product 1

HCID 89455725HCID 89455725, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxybenzoate (2.260 g, 6.29 mmol) in THF (25 ml), aqueous 1M LiOH (6.29 ml, 6.29 mmol) was added, and the reaction was stirred at RT for 6 hours. Additional 1M LiOH (12.58 ml, 12.58 mmol) was added over 3 days with stirring at the same temperature. The solvents were removed under vacuum, and the residue was partitioned between EtOAc and 2N HCl; the organic phase was dried over Na2SO4 and the solvent was removed. The crude was purified by chromatography on silica gel column (DCM:MeOH=98:2 to 9:1) to afford 3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-methoxybenzoic acid (1.240 g, 3.59 mmol, 57.1% yield, MS/ESI+ 368.0 [MHNa]+).

Workup

  1. stirringwith stirring at the same temperature
  2. customThe solvents were removed under vacuum
  3. customthe residue was partitioned between EtOAc and 2N HCl
  4. dry with materialthe organic phase was dried over Na2SO4
  5. customthe solvent was removed
  6. customThe crude was purified by chromatography on silica gel column (DCM:MeOH=98:2 to 9:1)

Sources & evidence

ORD record
ord-fb6b502309524d52a6f659fd74ecfdd2
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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