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Trifluoroacetic acid → Ethyl 7-[4-(aminomethyl)benzyloxy]-4-chloro-1-methyl-2-indolecarboxylate

HRID 565058
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HRID 565058 반응식
C(OC([NH:8][CH2:9][C:10]1[CH:33]=[CH:32][C:13]([CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([Cl:31])=[C:20]3[C:24]=2[N:23]([CH3:25])[C:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:21]3)=[CH:12][CH:11]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][CH2:9][C:10]1[CH:33]=[CH:32][C:13]([CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([Cl:31])=[C:20]3[C:24]=2[N:23]([CH3:25])[C:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:21]3)=[CH:12][CH:11]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 21194287HCID 21194287, 화합물

생성물 1

HCID 21194237Ethyl 7-[4-(aminomethyl)benzyloxy]-4-chloro-1-methyl-2-indolecarboxylate수율 101.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

A mixture of 0.75 g (1.59 mmol) of ethyl 7-[4-(tert-butoxycarbonylaminomethyl)benzyloxy]-4-chloro-1-methyl-2-indolecarboxylate, 5 ml of trifluoroacetic acid and 50 ml of dichloromethane was stirred at 0° C. for 2 hours. The reaction mixture was concentrated under reduced pressure. Thereafter ice water was poured onto the resulting residue and 28% aqueous ammonia was added thereto to render alkaline (pH=9 to 10). The mixture was then extracted three times with ethyl acetate. The combined extracts were washed with saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 0.60 g (>99%) of ethyl 7-[4-(aminomethyl)benzyloxy]-4-chloro-1-methyl-2-indolecarboxylate.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThereafter ice water was poured onto the resulting residue and 28% aqueous ammonia
  3. additionwas added
  4. extractionThe mixture was then extracted three times with ethyl acetate
  5. washThe combined extracts were washed with saturated sodium chloride solution
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-b4304aaba68c46d7a0dceca3739f42b7
출처 데이터셋
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06169107A

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