Triethylamine → Methyl 2,2-dimethyl-3-[(methylsulfonyl)amino]propanoate

HRID 1992213Notes

Reaction equation

HRID 1992213 reaction equation
[NH2:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].CCN(CC)CC.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH3:8][C:3]([CH3:9])([CH2:2][NH:1][S:18]([CH3:17])(=[O:20])=[O:19])[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13285789Methyl 3-amino-2,2-dimethylpropanoate

Product 1

HCID 86608479Methyl 2,2-dimethyl-3-[(methylsulfonyl)amino]propanoateYield 31.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-amino-2,2-dimethylpropanoate (249 mg, 1.90 mmol) and Et3N (0.80 mL, 5.70 mmol) in 2 mL CH2Cl2 was added methanesulfonyl chloride (0.29 mL, 3.80 mmol). The reaction was stirred for 2 days, quenched by the addition of saturated aqueous NaHCO3, extracted with CHCl3, and chromatographed (1:1 hex:EtOAc) to provide methyl 2,2-dimethyl-3-[(methylsulfonyl)amino]propanoate (124 mg, 31%) as a clear oil. 1H NMR (400 MHz, CDCl3), 4.95 (t, 1H, J=6.8 Hz), 3.69 (s, 3H), 3.16 (d, 2H, J=6.8 Hz), 2.95 (s, 3H), 1.24 (s, 6H). Methyl 2,2-dimethyl-3-[(methylsulfonyl)amino]propanoate was hydrolyzed using aqueous NaOH to provide 2,2-dimethyl-3-[(methylsulfonyl)amino]propanoic acid, which was used without further purification. 1H NMR (400 MHz, CDCl3), δ 10.28 (br. s, 1H), 5.56 (br. s, 1H), 3.14 (s, 2H), 2.94 (s, 3H), 1.25 (5, 6H).

Workup

  1. customquenched by the addition of saturated aqueous NaHCO3
  2. extractionextracted with CHCl3
  3. customchromatographed (1:1 hex:EtOAc)

Sources & evidence

ORD record
ord-52b5b79f32be45c18dd34fa45ad39be5
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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