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Trifluoroacetic acid → (3R,6S)-1-(4-Fluoro-benzyl)-3,6-dimethyl-piperazine-2,5-dione

HRID 11607
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HRID 11607 반응식
CO[C:3](=O)[C@@H:4]([N:6]([C:15](=[O:26])[C@H:16]([NH:18][C:19](OC(C)(C)C)=[O:20])[CH3:17])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)C.FC(F)(F)C(O)=O>ClCCl>[F:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][N:6]2[C@@H:4]([CH3:3])[C:19](=[O:20])[NH:18][C@H:16]([CH3:17])[C:15]2=[O:26])=[CH:9][CH:10]=1
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참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 57016912(2S)-2-[(2R)-(2-Tert-Butoxycarbonylamino-Propionyl)-(4-Fluoro-Benzyl)-Amino]propionic Acid Methyl Ester

생성물 1

HCID 69325248(3R,6S)-1-(4-Fluoro-benzyl)-3,6-dimethyl-piperazine-2,5-dione수율 23%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (2S)-2-[(2R)-(2-tert-butoxycarbonylamino-propionyl)-(4-fluoro-benzyl)-amino]-propionic acid methyl ester (43 g, 382 mmol) in dichloromethane (120 mL) at 0° C. was added trifluoroacetic acid (60 mL). The reaction was allowed to warm to ambient temperature and stirred for 2 hours. The reaction was cooled to 0° C. and slowly quenched by addition of 3 N sodium hydroxide until basic. The resulting mixture was extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to give the title compound (22 g).

후처리

  1. temperatureThe reaction was cooled to 0° C.
  2. customslowly quenched by addition of 3 N sodium hydroxide until basic
  3. extractionThe resulting mixture was extracted with dichloromethane
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c843a15b5d714641a5db49ffbd9018c2
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07098212B2

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