반응 #3449

반응 방정식

[[3-(2-amino-1,2-dioxoethyl)-1-[(2,6-dichlorophenyl)methyl]-2-methyl-1H-indol-4-yl]oxy]acetic acid methyl ester

NaOH

MeOH

Ethyl acetate

→

[[3-(2-amino-1,2-dioxoethyl)-1-[(2,6-dichlorophenyl)methyl]-2-methyl-1H-indol-4-yl]oxy]acetic acid

수율 86.0%

용매

water

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도to maintain
3. 3
   온도reflux for 0.17 hours
4. 4
   기타the aqueous layer separated
5. 5
   추출the mixture extracted with ethyl acetate two times
6. 6
   여과The part that was not soluble was filtered
7. 7
   건조The filtrate was dried (MgSO4)
8. 8
   농축concentrated
9. 9
   세척The remaining solid was washed with a small volume of ether/methylene chloride
10. 10
    여과the insoluble material filtered

실험 절차

A mixture of 420 mg (0.94 mmol) of [[3-(2-amino-1,2-dioxoethyl)-1-[(2,6-dichlorophenyl)methyl]-2-methyl-1H-indol-4-yl]oxy]acetic acid methyl ester, 5 mL of 1N NaOH and 15 mL of MeOH was heated to maintain reflux for 0.17 hours, cooled to room temperature and stirred 0.5 hours. Ethyl acetate and water was added, the aqueous layer separated, made acidic to pH 2-3 with 1N HCl, and the mixture extracted with ethyl acetate two times. The part that was not soluble was filtered. The filtrate was dried (MgSO4) and concentrated. The remaining solid was washed with a small volume of ether/methylene chloride and the insoluble material filtered and combined with the filtered material above to give 351 mg (86% yield) of [[3-(2-amino-1,2-dioxoethyl)-1-[(2,6-dichlorophenyl)methyl]-2-methyl-1H-indol-4-yl]oxy]acetic acid, mp, 236°-239° C.

출처