Lithium Hydroxide → HCID 86679465, compound

HRID 1776512Notes

Reaction equation

HRID 1776512 reaction equation
[Li+].[OH-].[C:3]([O:7][C:8]([N:10]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1)[S:11]([CH2:14][C:15]([O:17]C)=[O:16])(=[O:13])=[O:12])=[O:9])([CH3:6])([CH3:5])[CH3:4].CCOC(C)=O>O.C1COCC1>[C:3]([O:7][C:8]([N:10]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1)[S:11]([CH2:14][C:15]([OH:17])=[O:16])(=[O:13])=[O:12])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 86679463HCID 86679463, compound

Product 1

HCID 86679465HCID 86679465, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH (28.1 mg, 0.669 mmol) in water (0.66 ml) was added to a solution of methyl 2-(N-(tert-butoxycarbonyl)-N-(3,4-dimethoxyphenyl)sulfamoyl)-acetate (237 mg, 0.609 mmol) in THF (3 ml), and the mixture was stirred at RT for 2 hours. EtOAc was added, and the solution was washed with HCl 1N (6 ml); the organic phase was washed with brine, dried over Na2SO4, filtered and evaporated, to give 2-(N-(tert-butoxycarbonyl)-N-(3,4-dimethoxyphenyl)sulfamoyl)acetic acid (200 mg, 0.533 mmol, 88% yield, MS/ESI+ 397.9 [MNa]+) that was used in the next step without further purification.

Workup

  1. washthe solution was washed with HCl 1N (6 ml)
  2. washthe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-a56c6fdd9a7844adbcd6d20f9145ed82
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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