Water → Methyl-2-(4-acetylphenylsulfonamido)-2-methylpropanoate

HRID 1519106Notes

Reaction equation

HRID 1519106 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C:5]([NH2:8])([CH3:7])[CH3:6].[C:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1)(=[O:12])[CH3:11].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:9])[C:5]([NH:8][S:19]([C:16]1[CH:15]=[CH:14][C:13]([C:10](=[O:12])[CH3:11])=[CH:18][CH:17]=1)(=[O:21])=[O:20])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2664184-Acetylbenzenesulfonyl chlorideHCID 13258034Methyl 2-aminoisobutyrate hydrochloride

Product 1

HCID 60744560Methyl-2-(4-acetylphenylsulfonamido)-2-methylpropanoateYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

methyl-2-amino-2-methylpropanoate hydrochloride (2 g, 13.07 mmol) was dissolved in CH2Cl2 (50 ml), and added with 4-acetylbenzene-1-sulfonyl chloride (2.86 g, 13.07 mmol) and triethylamine (7.2 ml, 52.27 mmol), followed by stirring 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-2-(4-acetylphenylsulfonamido)-2-methylpropanoate (2.55 g, 8.52 mmol, 56%).

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-8a46ac300c1f40b5bb2d83b5a985c7e5
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

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