反応 #48843

反応方程式

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

溶媒

DMF

反応条件

後処理

1. 1
   その他The DMF was removed in vacuo
2. 2
   workup.ADDITIONWater (100 mL) was added
3. 3
   抽出the mixture extracted with ethyl acetate (3×50 mL)
4. 4
   洗浄washed with brine (100 mL)
5. 5
   乾燥The solution was dried (MgSO4)
6. 6
   ろ過filtered
7. 7
   その他evaporated in vacuo
8. 8
   その他to give the crude product which
9. 9
   その他was chromatographed on silica
10. 10
    洗浄eluting with a gradient of 50-100% ethyl acetate in isohexane

実験手順

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).

出典