反应详情

To a 0° C. suspension of 4-cyclopropoxybenzoic acid (24.5 g, 137.3 mmol) in dichloromethane (350 mL) containing 2 drops of DMF, slowly add oxalyl chloride (23.8 mL, 274.7 mmol). After addition, remove the cooling bath and stir for 2 hours. Concentrate the material to dryness under reduced pressure. Dissolve the residue in dichloromethane (500 mL), and then add ethyl 1-aminocyclopropanecarboxylate hydrochloride (Indofine #04-265, 24.9 g, 150.5 mmol) and triethylamine (57.2 mL, 410.4 mmol). Stir the mixture at ambient temperature for approximately 16 hours. Wash the mixture once with 10% NaHSO4 (250 mL). Separate the organic portion and extract the aqueous portion 2× with dichloromethane (200 mL). Combine the organic, dry over sodium sulfate, filter, and concentrate under reduced pressure. Purify the crude mixture by flash chromatography (0% to 45% EtOAc/Hex) to give the title compound (33.7 g, 85%): MS (m/z): 290 (M+1).

1. additionAfter addition
2. customremove the cooling bath
3. concentrationConcentrate the material to dryness under reduced pressure
4. dissolutionDissolve the residue in dichloromethane (500 mL)
5. stirringStir the mixture at ambient temperature for approximately 16 hours
6. washWash the mixture once with 10% NaHSO4 (250 mL)
7. customSeparate the organic portion
8. extractionextract the aqueous portion 2× with dichloromethane (200 mL)
9. dry with materialCombine the organic, dry over sodium sulfate
10. filtrationfilter
11. concentrationconcentrate under reduced pressure
12. customPurify the crude mixture by flash chromatography (0% to 45% EtOAc/Hex)