反応 #42906

反応方程式

HCl

EtOAc

1-(tert-butoxycarbonylamino-methyl)-6,8-dimethoxy-isoquinoline-4-carboxylic acid ethyl ester

LiOH—H2O

→

1-(tert-butoxycarbonylamino-methyl)-6,8-dimethoxy-isoquinoline-4-carboxylic acid

収率 96.0%

溶媒

water

THF

H2O

反応条件

後処理

1. 1
   workup.WAITat then at room temperature for 18 hours
2. 2
   その他The layers were then separated
3. 3
   抽出the aqueous phase was extracted with EtOAc
4. 4
   洗浄The combined organic layers were then washed with brine
5. 5
   乾燥dried over magnesium sulfate
6. 6
   ろ過filtered
7. 7
   その他The solvent was removed under reduced pressure

実験手順

To a solution of 1-(tert-butoxycarbonylamino-methyl)-6,8-dimethoxy-isoquinoline-4-carboxylic acid ethyl ester (520 mg, 1.34 mmol) in THF (10 ml) and H2O (10 ml) under nitrogen, LiOH—H2O (95 mg, 2.3 mmol) was added. The reaction was stirred at 50° C. for 3.5 hours and at then at room temperature for 18 hours. EtOAc and water were then added and the pH was adjusted to 5 by dropwise addition of 6N HCl. The layers were then separated and the aqueous phase was extracted with EtOAc. The combined organic layers were then washed with brine, dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure to give 1-(tert-butoxycarbonylamino-methyl)-6,8-dimethoxy-isoquinoline-4-carboxylic acid as a solid (464 mg, 96%). H1-NMR (DMSO): δ, 8.84 (s, 1H), 7.96 (s, 1H), 6.91 (t, 1H, J=5.4 Hz), 6.77 (s, 1H), 4.80 (d, 2H, J=5.43 Hz), 3.95 and 3.88 (s, 3H each), 1.36 (s, 9H).

出典