Triethylamine → HCID 86608477, compound

HRID 1992200Notes

Reaction equation

HRID 1992200 reaction equation
[NH2:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].CCN(CC)CC.[CH:17]([S:20](Cl)(=[O:22])=[O:21])([CH3:19])[CH3:18]>C(Cl)Cl>[CH:17]([S:20]([NH:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5])(=[O:22])=[O:21])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 13285789Methyl 3-amino-2,2-dimethylpropanoate

Product 1

HCID 86608477HCID 86608477, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

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-d90617ff7d324340b612a735981f48da
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

Loading…