Lithium Hydroxide → HCID 86679534, compound

HRID 1776581Notes

Reaction equation

HRID 1776581 reaction equation
[C:1]([O:5][C:6]([O:8][C:9]1[CH:18]=[CH:17][C:16]([N:19]([CH2:24][CH:25]2[CH2:27][CH2:26]2)[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][C:10]=1[C:11]([O:13]C)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>C1COCC1>[C:1]([O:5][C:6]([O:8][C:9]1[CH:18]=[CH:17][C:16]([N:19]([CH2:24][CH:25]2[CH2:26][CH2:27]2)[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][C:10]=1[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86679533HCID 86679533, compound

Product 1

HCID 86679534HCID 86679534, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(tert-butoxycarbonyloxy)-5-(N-(cyclopropylmethyl)-methylsulfonamido)benzoate (6 g, 15.02 mmol) was dissolved in THF (50 ml); LiOH 2M (15.02 ml, 30.0 mmol) was added; and the mixture was stirred at RT for 24 hours. The volatiles were removed under vacuum, and the residue was dissolved in water, neutralized with HCl 1M (pH 6) and extracted with EtOAc. The organic layer was dried over Na2SO4 and evaporated to dryness. The resulting crude was purified by flash chromatography on silica gel column (DCM:MeOH=10:0.5) affording 2-(tert-butoxycarbonyloxy)-5-(N-(cyclopropylmethyl)methylsulfonamido)benzoic acid (3 g, 7.78 mmol, 51.8% yield, MS/ESI+ 407.9 [MNa]+).

Workup

  1. customThe volatiles were removed under vacuum
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated to dryness
  6. customThe resulting crude was purified by flash chromatography on silica gel column (DCM:MeOH=10:0.5)

Sources & evidence

ORD record
ord-85494611d44f4b12bb8f29867e192da6
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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