Sodium Hydroxide → 2,2-Dimethyl-3-[(methylsulfonyl)amino]propanoic acid
Reaction equation
[CH3:1][C:2]([CH3:13])([CH2:7][NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:3]([O:5]C)=[O:4].[OH-].[Na+]>>[CH3:1][C:2]([CH3:13])([CH2:7][NH:8][S:9]([CH3:12])(=[O:10])=[O:11])[C:3]([OH:5])=[O:4]Participants
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).
Sources & evidence
- ORD record
- ord-1b2e38fccd6e45eeb7e9102518395ebb
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07645771B2
Reaction notes
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