Methanol → HCID 71246760, compound

HRID 1519093Notes

Reaction equation

HRID 1519093 reaction equation
C[O:2][C:3](=[O:22])[C:4]([CH3:21])([N:6]([CH3:20])[S:7]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2)(=[O:9])=[O:8])[CH3:5].C1COCC1.CO.O[Li].O>O>[CH3:21][C:4]([N:6]([CH3:20])[S:7]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2)(=[O:8])=[O:9])([CH3:5])[C:3]([OH:22])=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 71246507HCID 71246507, compound

Product 1

HCID 71246760HCID 71246760, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

methyl-2-methyl-2-(N-methylquinoline-8-sulfonamido)propanoate (650 mg, 2.01 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, adjusted with 2N—HCl to pH 5-6, 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-methyl-2-(N-methylquinoline-8-sulfonamido)propionic acid (610 mg, 1.97 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-a02f579e061444139bce3c1f77ffa164
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

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