反応 #714937

反応方程式

ammonium chloride

sodium hydride

cyclopropane

THF

tert-butyl N-[(4aR,11bR)-10-[(5-chloropyrazine-2-carbonyl)amino]-3,3,11b-trimethyl-4,4-dioxo-5,6-dihydro-4aH-[1]benzoxepino[4,5-b][1,4]thiazin-2-yl]carbamate

THF

→

title compound

収率 83.0%

tert-butyl N-[(4aR,11bR)-10-[[5-(cyclopropylmethoxy)pyrazine-2-carbonyl]amino]-3,3,11b-trimethyl-4,4-dioxo-5,6-dihydro-4aH-[1]benzoxepino[4,5-b][1,4]thiazin-2-yl]carbamate

収率 83.0%

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction was stirred at ambient temperature for 1 hour
2. 2
   抽出extracted with ethyl acetate
3. 3
   濃縮The organic portion was concentrated
4. 4
   その他The resulting crude was purified by column chromatography
5. 5
   洗浄eluting with 10-50% ethyl acetate/heptane

実験手順

A solution of hydroxymethyl)cyclopropane (0.10 mL, 1.20 mmol) in THF (1.4 mL) was cooled to 0° C. and treated with sodium hydride (60% wt; 36.1 mg, 0.90 mmol). The reaction was stirred for 30 minutes and then a solution of tert-butyl N-[(4aR,11bR)-10-[(5-chloropyrazine-2-carbonyl)amino]-3,3,11b-trimethyl-4,4-dioxo-5,6-dihydro-4aH-[1]benzoxepino[4,5-b][1,4]thiazin-2-yl]carbamate (113 mg, 0.20 mmol) in 1 mL of THF was added. The reaction was stirred at ambient temperature for 1 hour. The reaction was treated with aqueous ammonium chloride and extracted with ethyl acetate. The organic portion was concentrated. The resulting crude was purified by column chromatography, eluting with 10-50% ethyl acetate/heptane to afford the title compound (100 mg, 0.17 mmol, 83%) as an off-white solid. MS m/z=600.2 (M+H).

出典