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(2-{2-[(2R)-2-carbamoylmethyl-4-(4-fluoro-benzyl)-piperazin-1-yl]-2-oxo-ethoxy}-5-chloro-phenoxy)-acetic Acid tert-butyl Ester → (2-{2-[(2R)-2-Carbamoylmethyl-4-(4-fluoro-benzyl)-piperazin-1-yl]-2-oxo-ethoxy}-5-chloro-phenoxy)-acetic Acid

HRID 11708
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HRID 11708 반응식
C([O:5][C:6](=[O:38])[CH2:7][O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[O:16][CH2:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH2:22][C@H:21]1[CH2:34][C:35](=[O:37])[NH2:36])=[O:19])(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[C:35]([CH2:34][C@@H:21]1[CH2:22][N:23]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH2:24][CH2:25][N:20]1[C:18](=[O:19])[CH2:17][O:16][C:10]1[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=1[O:8][CH2:7][C:6]([OH:38])=[O:5])(=[O:37])[NH2:36]
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참가 물질

4

반응물 1

HCID 69656159(2-{2-[(2R)-2-carbamoylmethyl-4-(4-fluoro-benzyl)-piperazin-1-yl]-2-oxo-ethoxy}-5-chloro-phenoxy)-acetic Acid tert-butyl Ester

생성물 1

HCID 69655813(2-{2-[(2R)-2-Carbamoylmethyl-4-(4-fluoro-benzyl)-piperazin-1-yl]-2-oxo-ethoxy}-5-chloro-phenoxy)-acetic Acid수율 84.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매

실험 절차

A solution of (2-{2-[(2R)-2-carbamoylmethyl-4-(4-fluoro-benzyl)-piperazin-1-yl]-2-oxo-ethoxy}-5-chloro-phenoxy)-acetic acid tert-butyl ester (0.070 g, 0.13 mmol) in dichloromethane (1 mL) and trifluoroacetic acid (0.10 mL) was stirred for 3.5 h and then concentrated. The resulting residue was diluted with dichloromethane and the excess trifluoroacetic acid was quenched with saturated aqueous sodium carbonate. The aqueous layer was neutralized with 0.1N hydrochloric acid and extracted one time with dichloromethane/methanol (1:1) and twice with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated to give the title compound (0.054 g, LRMS: 492.4, 494.4).

후처리

  1. concentrationconcentrated
  2. additionThe resulting residue was diluted with dichloromethane
  3. customthe excess trifluoroacetic acid was quenched with saturated aqueous sodium carbonate
  4. extractionextracted one time with dichloromethane/methanol (1:1)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b8291b8cd8d0474b89c2e338ba9e10a5
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07098212B2

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