تفاعل #42906

معادلة التفاعل

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

المردود 96.0%

المذيبات

water

THF

H2O

ظروف التفاعل

المعالجة

1. 1
   workup.WAITat then at room temperature for 18 hours
2. 2
   أخرىThe layers were then separated
3. 3
   استخلاصthe aqueous phase was extracted with EtOAc
4. 4
   غسيلThe combined organic layers were then washed with brine
5. 5
   تجفيفdried over magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   أخرىThe solvent was removed under reduced pressure

الإجراء التجريبي

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).

المصدر