Hydrochloric Acid → 3-[(Methoxycarbonyl)amino]butanoic acid

Methyl chloroformate (0.071 mL, 0.91 mmol) was added to a solution of ethyl 3-aminobutanoate (0.10 g, 0.76 mmol) (Aldrich, Cat. #E10556) and triethylamine (0.16 mL, 1.1 mmol) in tetrahydrofuran (2.0 mL) at r.t. After stirring at r.t. for 30 min, the mixture was diluted with water, and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was dissolved in methanol (3.0 mL) and water (1.0 mL). To the solution was added lithium hydroxide monohydrate (0.049 g, 1.2 mmol). The reaction mixture was stirred at r.t. overnight. The mixture was adjusted to pH=2 with aqueous HCl, and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated to afford the desired product.

1. extractionextracted with ethyl acetate (3×10 mL)
2. dry with materialThe combined organic layers were dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. dissolutionThe residue was dissolved in methanol (3.0 mL)
6. stirringThe reaction mixture was stirred at r.t. overnight
7. extractionextracted with ethyl acetate (3×10 mL)
8. dry with materialThe combined organic layers were dried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-ddff6cff70424a10861e859c93330974

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481732B2