Water → HCID 71246852, compound

HRID 1519091Notes

Reaction equation

HRID 1519091 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C:5]([NH2:8])([CH3:7])[CH3:6].[N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[S:20](Cl)(=[O:22])=[O:21])[CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.O>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:9])[C:5]([CH3:7])([NH:8][S:20]([C:18]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:19]=1[N:10]=[CH:11][CH:12]=[CH:13]2)(=[O:21])=[O:22])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 292208-Quinolinesulfonyl chlorideHCID 13258034Methyl 2-aminoisobutyrate hydrochloride

Product 1

HCID 71246852HCID 71246852, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

methyl-2-amino-2-methylpropanoate hydrochloride (5 g, 32.6 mmol) was dissolved in CH2Cl2 (110 ml), added with quinoline-8-sulfonyl chloride (8.18 g, 35.9 mmol) and triethylamine (18 ml, 130.6 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-2-methyl-2-(quinoline-8-sulfonamido)propanoate (8.74 g, 32.8 mmol, 95%).

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-8420f241ea974f2389a570b8034cb324
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

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