Methanol → HCID 65663729, compound

HRID 1519096Notes

Reaction equation

HRID 1519096 reaction equation
C[O:2][C:3](=[O:20])[C:4]([N:7]([CH2:18][CH3:19])[S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])(=[O:10])=[O:9])([CH3:6])[CH3:5].C1COCC1.CO.O[Li].O>O>[CH2:18]([N:7]([C:4]([CH3:5])([CH3:6])[C:3]([OH:20])=[O:2])[S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])(=[O:10])=[O:9])[CH3:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 71246883HCID 71246883, compound

Product 1

HCID 65663729HCID 65663729, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

methyl-2-(N-ethyl-2-methylphenylsulfonamido)-2-methylpropanoate (524 mg, 1.75 mmol) was charged, and dissolved through addition of THF (5 ml), and methanol (5 ml). LiOH.H2O dissolved in H2O (5 ml) was added thereto, followed by stirring for 12 hours at room temperature. After stirring for 12 hours, the resultant solution was vacuum-evaporated, acidified with 2N—HCl to pH 2-3, and extracted with EA (×2). The organic layer was dried with MgSO4, and filtered. Through vacuum distillation, the solvent was removed so as to obtain 2-(N-ethyl-2-methylphenylsulfonamido)-2-methylpropionic acid (490 mg, 1.72 mmol, 98%).

Workup

  1. additionwas added
  2. stirringAfter stirring for 12 hours
  3. customthe resultant solution was vacuum-evaporated
  4. extractionextracted with EA (×2)
  5. dry with materialThe organic layer was dried with MgSO4
  6. filtrationfiltered
  7. distillationThrough vacuum distillation
  8. customthe solvent was removed so as

Sources & evidence

ORD record
ord-ec5ed5eafa4e4dcead371f4537cdb95e
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

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