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Acetyl chloride → N-[1-[4-[(3-fluorophenyl)methoxy]phenyl]-5-oxopyrrolidin-3-yl]acetamide

HRID 859205
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인쇄 미리보기

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HRID 859205 반응식
Cl.[NH2:2][CH:3]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)=[CH:10][CH:9]=2)[C:5](=[O:23])[CH2:4]1.C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32].[OH-].[NH4+]>ClCCl>[F:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([N:6]2[C:5](=[O:23])[CH2:4][CH:3]([NH:2][C:31](=[O:33])[CH3:32])[CH2:7]2)=[CH:13][CH:12]=1
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참가 물질

6

반응물 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 68614460(RS)-4-amino-1-[4-(3-fluoro-benzyloxy)-phenyl]-pyrrolidin-2-one hydrochloride

생성물 1

HCID 9927995N-[1-[4-[(3-fluorophenyl)methoxy]phenyl]-5-oxopyrrolidin-3-yl]acetamide수율 83.5%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

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온도
0 °C

실험 절차

A solution of 25 mg (0.07 mmol) of (RS)-4-amino-1-[4-(3-fluoro-benzyloxy)-phenyl]-pyrrolidin-2-one hydrochloride in 1 ml of dichloromethane is treated with 22 μl (0.16 mmol) of triethylamine and cooled to 0° C. To this solution, 6 μl (0.08 mmol) of acetylchloride are added and stirring at 0° C. is continued for 30 min. For the working-up, the reaction mixture is treated with 2 ml of ammonium hydroxide solution, the organic phase separated, thereafter dried over sodium sulfate and evaporated under reduced pressure. For purification, the material obtained is chromatographed on silica gel using a 95:5 mixture of dichloromethane and methanol as the eluent. There are obtained 20 mg (78% of theory) of (RS)-N-{1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidin-3-yl}-acetamide as a white solid. MS: m/e=343 (M+H)+.

후처리

  1. customthe organic phase separated
  2. dry with materialdried over sodium sulfate
  3. customevaporated under reduced pressure
  4. customFor purification
  5. customthe material obtained
  6. customis chromatographed on silica gel using
  7. additiona 95:5 mixture of dichloromethane and methanol as the eluent

출처 및 근거

ORD 기록
ord-75d714352253457bbc316bb6f8e816d2
출처 데이터셋
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07151111B2

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