Methanol → Methyl-1-(2-nitrophenylsulfonamido)cyclobutanecarboxylic acid

HRID 1519082Notes

Reaction equation

HRID 1519082 reaction equation
C[O:2][C:3]([C:5]1([NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])[CH2:8][CH2:7][CH2:6]1)=[O:4].[CH2:22]1COCC1.CO.O[Li].O>O>[CH3:22][CH:6]1[CH2:7][CH2:8][C:5]1([NH:9][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])[C:3]([OH:2])=[O:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 71246328Methyl-1-(2-nitrophenylsulfonamido)cyclobutanecarboxylate

Product 1

HCID 71246330Methyl-1-(2-nitrophenylsulfonamido)cyclobutanecarboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

methyl-1-(2-nitrophenylsulfonamido)cyclobutanecarboxylate (500 mg, 1.59 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, acidified with 2N—HCl to pH 2-3, 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 methyl-1-(2-nitrophenylsulfonamido)cyclobutanecarboxylic acid (468 mg, 1.56 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-41cd01ea6aeb42d083e8b7b81b9e89ce
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

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