Methanol → HCID 43361589, compound

HRID 1519085Notes

Reaction equation

HRID 1519085 reaction equation
C[O:2][C:3]([C:5]1([NH:10][S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=2[CH3:21])(=[O:13])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].C1COCC1.CO.O[Li].O>O>[Cl:20][C:16]1[C:15]([CH3:21])=[C:14]([S:11]([NH:10][C:5]2([C:3]([OH:4])=[O:2])[CH2:9][CH2:8][CH2:7][CH2:6]2)(=[O:13])=[O:12])[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 71247066HCID 71247066, compound

Product 1

HCID 43361589HCID 43361589, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

methyl-1-(3-chloro-2-methylphenylsulfonamido)cyclopentanecarboxylate (550 mg, 1.65 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 the 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. Then, through vacuum distillation, the solvent was removed so as to obtain 1-(3-chloro-2-methylphenylsulfonamido)cyclopentanecarboxylic acid (516 mg, 1.62 mmol, 98%).

Workup

  1. additionwas added
  2. waitAfter the 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. distillationThen, through vacuum distillation
  8. customthe solvent was removed so as

Sources & evidence

ORD record
ord-93298d285dd14ea48c852de49ccff3b2
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

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