반응 #48878

반응 방정식

DIPEA

3-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)benzoic acid

HATU

2-amino-1,3 thiazole

→

desired compound

수율 99.9%

3-[4-(Azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-1,3-thiazol-2-ylbenzamide

수율 99.9%

용매

water

DMF

반응 조건

후처리

1. 1
   추출the mixture extracted with ethyl acetate
2. 2
   세척washed with brine
3. 3
   건조dried (MgSO4)
4. 4
   여과filtered
5. 5
   기타evaporated in vacuo
6. 6
   기타to give the crude product which
7. 7
   기타was chromatographed on silica
8. 8
   세척eluting with 75% ethyl acetate in isohexane

실험 절차

DIPEA (0.5 mL, 3.0 mmol) was added to a suspension of 3-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)benzoic acid (503 mg, 1.0 mmol), HATU (495 mg, 1.3 mmol) and 2-amino-1,3 thiazole (300 mg, 3.0 mmol) in DMF (6 mL). The resulting mixture was stirred at RT for 16 hours, water (90 mL) was added and the mixture extracted with ethyl acetate. The extracts were combined, washed with brine, dried (MgSO4), filtered and evaporated in vacuo to give the crude product which was chromatographed on silica, eluting with 75% ethyl acetate in isohexane, to give the desired compound (585 mg).

출처