Methanol → 5-acetamido-1H-indole-2-carboxylic Acid

HRID 1874829노트

반응식

HRID 1874829 반응식
[OH-].[Li+].[C:3]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12](C(OCCC(C)(C)C)=O)[C:11]([C:25]([O-:27])=[O:26])=[CH:10]2)(=[O:5])[CH3:4].CO.O>C1COCC1>[C:3]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:25]([OH:27])=[O:26])=[CH:10]2)(=[O:5])[CH3:4]

참가 물질

6

반응물 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 867616451-(1,1-dimethylethyl)2-ethyl 5-(acetylamino)-1H-indole-1,2-dicarboxylate

생성물 1

HCID 107751705-acetamido-1H-indole-2-carboxylic Acid수율 43%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

Lithium hydroxide (0.028 g, 1.184 mmol) was added to a solution of 1-(1,1-dimethylethyl)2-ethyl 5-(acetylamino)-1H-indole-1,2-dicarboxylate (0.041 g, 0.118 mmol) in THF:MeOH:water/3:1:1. The reaction mixture was heated at 50° C. for 1 h. The solvent was evaporated. The residue was dissolved in water, acidified with 6N aqueous HCl and extracted with dichloromethane. A solid formed in the aqueous layer which was collected by filtration and dried to give the title compound (0.011 g, 43%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 12.85 (s, 1H), 11.63 (s, 1H), 9.79 (s, 1H), 7.97 (s, 1H), 7.22-7.38 (m, 2H), 7.01 (s, 1H), 2.01 (s, 3H). MS: m/z 219 (M+1).

후처리

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with dichloromethane
  4. customA solid formed in the aqueous layer which
  5. filtrationwas collected by filtration
  6. customdried

출처 및 근거

ORD 기록
ord-1c71022b3f0046cc8e2113237c7c4923
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

반응 노트

불러오는 중…