Sodium Hydroxide → HCID 86608478, compound

HRID 1992201Notes

Reaction equation

[CH:1]([S:4]([NH:7][CH2:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12]C)=[O:11])(=[O:6])=[O:5])([CH3:3])[CH3:2].[OH-].[Na+]>>[CH:1]([S:4]([NH:7][CH2:8][C:9]([CH3:15])([CH3:14])[C:10]([OH:12])=[O:11])(=[O:5])=[O:6])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 86608477HCID 86608477, compound

Product 1

HCID 86608478HCID 86608478, compound

Procedure

To a solution of methyl 3-amino-2,2-dimethylpropanoate (200 mg, 1.53 mmol) and Et3N (0.64 mL, 4.59 mmol) in 2 mL CH2Cl2 was added isopropylsulfonyl chloride (0.34 mL, 3.05 mmol). The reaction was stirred for 24 h, quenched by the addition of saturated aqueous NaHCO3, extracted with CHCl3, and chromatographed (1:1 hex:EtOAc) to provide methyl 3-[(isopropylsulfonyl)amino]-2,2-dimethylpropanoate (77 mg, 21%) as a solid. 1H NMR (400 MHz, CDCl3), 4.78 (t, 1H, J=6.6 Hz), 3.68 (s, 3H), 3.20-3.11 (m, 3H), 1.36 (d, 6H, J=6.9 Hz), 1.23 (s, 6H). Methyl 3-[(isopropylsulfonyl)amino]-2,2-dimethylpropanoate was hydrolyzed using aqueous NaOH to provide 3-[(isopropylsulfonyl)amino]-2,2-dimethylpropanoic acid, which was used without further purification.

Sources & evidence

ORD record: ord-70e4c7df93a443588efe39eed0a186ca
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645771B2

Reaction notes

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