Water → HCID 58870274, compound

HRID 1519095Notes

Reaction equation

HRID 1519095 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C:5]([NH2:8])(C)[CH3:6].C[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17](Cl)(=[O:19])=[O:18].[CH2:21](N(CC)CC)C.O>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:9])[CH:5]([N:8]([CH3:21])[S:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:11]=1)(=[O:19])=[O:18])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 13258034Methyl 2-aminoisobutyrate hydrochloride

Product 1

HCID 58870274HCID 58870274, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

methyl-2-amino-2-methylpropanoate hydrochloride (2 g, 13.1 mmol) was dissolved in CH2Cl2 (50 ml), and added with 2-methylbenzene-1-sulfonylchloride (2.74 g, 14.4 mmol) and triethylamine (14 ml, 52.4 mmol), followed by stirring for 12 hours at room temperature. 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-(methylphenylsulfonamido)propanoate (3.2 g, 11.7 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-3670db31f4084309be9a6c7517d8499a
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

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