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3-Isoxazolecarboxylic acid, 5-[(1R)-1-[[(1,1-diMethylethoxy)carbonyl]aMino]ethyl]-, ethyl ester synthesis
- Product Name:3-Isoxazolecarboxylic acid, 5-[(1R)-1-[[(1,1-diMethylethoxy)carbonyl]aMino]ethyl]-, ethyl ester
- CAS Number:893444-15-0
- Molecular formula:C13H20N2O5
- Molecular Weight:284.31
Yield:893444-15-0 75%
Reaction Conditions:
with triethylamine in N,N-dimethyl-formamide at 90; for 1.5 h;
Steps:
1
To compound 1.10 (6.7 g, 39.6 mmol) and 2-chloro-2- hydroxyiminoacetic acid ethyl ester (18.1 g, 120 mmol) in DMF at 9O0C (120 mL) was added Et3N (16.8 mL, 120 mmol) dropwise over 1 hour. The reaction mixture was stirred for 30 minutes, cooled to room temperature, and then concentrated in vacuo. The residue was dissolved in ethyl acetate and H2O. The aqueous layer was extracted with ethyl acetate (2X); the combined organic layer was extracted with 1N HCl, dried over NaHSO4, and concentrated in vacuo. Purification by silica gel chromatography (6:1 -> 3:1 hexanes / ethyl acetate) provided compound 1.11 (8.45 g, 75%).
References:
WO2006/65703,2006,A1 Location in patent:Page/Page column 97