반응 #48843

반응 방정식

DIPEA

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

HATU

2-amino-5-methylthiazole

→

desired compound

3-(Benzyloxy)-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(5-methyl-1,3-thiazol-2-yl)benzamide

용매

DMF

반응 조건

후처리

1. 1
   기타The DMF was removed in vacuo
2. 2
   workup.ADDITIONWater (100 mL) was added
3. 3
   추출the mixture extracted with ethyl acetate (3×50 mL)
4. 4
   세척washed with brine (100 mL)
5. 5
   건조The solution was dried (MgSO4)
6. 6
   여과filtered
7. 7
   기타evaporated in vacuo
8. 8
   기타to give the crude product which
9. 9
   기타was chromatographed on silica
10. 10
    세척eluting with a gradient of 50-100% ethyl acetate in isohexane

실험 절차

DIPEA (7.5 mL) was added to a suspension of 3-{(phenylmethyl)oxy}-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)benzoic acid (4.5 g, 0.011 mol), HATU (8.6 g, 0.023 mol) and 2-amino-5-methylthiazole (2.46 g, 0.022 mol) in DMF (70 mL). The resulting mixture was stirred at ambient temperature for 72 hours. The DMF was removed in vacuo. Water (100 mL) was added and the mixture extracted with ethyl acetate (3×50 mL). The extracts were combined and washed with brine (100 mL). The solution was dried (MgSO4), filtered, and evaporated in vacuo to give the crude product which was chromatographed on silica, eluting with a gradient of 50-100% ethyl acetate in isohexane, to give the desired compound. (1.7 g).

출처