Water → Methyl-1-(2-nitrophenylsulfonamido)cyclobutanecarboxylate

HRID 1519081Notes

Reaction equation

HRID 1519081 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1([NH2:10])[CH2:9][CH2:8][CH2:7]1)=[O:5].[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20](Cl)(=[O:22])=[O:21])([O-:13])=[O:12].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:2][O:3][C:4]([C:6]1([NH:10][S:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N+:11]([O-:13])=[O:12])(=[O:21])=[O:22])[CH2:9][CH2:8][CH2:7]1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 42614147Methyl 1-aminocyclobutane-1-carboxylate hydrochloride

Product 1

HCID 71246328Methyl-1-(2-nitrophenylsulfonamido)cyclobutanecarboxylateYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

methyl-1-aminocyclobutanecarboxylate hydrochloride (300 mg, 1.81 mmol) was dissolved in CH2Cl2 (7 ml), added with 2-nitrobenzene-1-sulfonyl chloride (441 mg, 1.99 mmol) and triethylamine (1 ml, 7.24 mmol) and stirred at room temperature for 12 hours. The resultant solution was added with H2O, extracted with CH2Cl2 (×2), dried with MgSO4, and filtered. Through vacuum distillation, the solvent was removed. The resultant mixture was purified with column chromatography so as to obtain methyl-1-(2-nitrophenylsulfonamido)cyclobutanecarboxylate (512 mg, 1.63 mmol, 90%).

Workup

  1. extractionextracted with CH2Cl2 (×2)
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. distillationThrough vacuum distillation
  5. customthe solvent was removed
  6. customThe resultant mixture was purified with column chromatography so as

Sources & evidence

ORD record
ord-1dea1569345042fbb9330c3ac598ac71
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

Loading…