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Acetic Acid → (3-{(R)-3-[(2-Chloro-3-trifluoromethyl-benzyl)-((S)-2-phenyl-propyl)-amino]-butoxy}-phenyl)-acetic Acid Methyl Ester

HRID 902673
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HRID 902673 반응식
[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][C@H:14]([NH:16][CH2:17][C@H:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:19])[CH3:15])[CH:6]=1.C(O)(=O)C.[Cl:31][C:32]1[C:39]([C:40]([F:43])([F:42])[F:41])=[CH:38][CH:37]=[CH:36][C:33]=1[CH:34]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.CCCCCC.O>[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][C@H:14]([N:16]([CH2:34][C:33]2[CH:36]=[CH:37][CH:38]=[C:39]([C:40]([F:41])([F:43])[F:42])[C:32]=2[Cl:31])[CH2:17][C@H:18]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH3:19])[CH3:15])[CH:6]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 27366722-Chloro-3-(trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69254631{3-[(R)-3-((S)-2-Phenyl-propylamino)-butoxy]-phenyl}-acetic Acid Methyl Ester

생성물 1

HCID 69252464(3-{(R)-3-[(2-Chloro-3-trifluoromethyl-benzyl)-((S)-2-phenyl-propyl)-amino]-butoxy}-phenyl)-acetic Acid Methyl Ester수율 40%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8058Hexane용매

실험 절차

To a solution of {3-[(R)-3-((S)-2-Phenyl-propylamino)-butoxy]-phenyl}-acetic acid methyl ester (0.12 g, 0.34 mmol) in dry dichloromethane was added acetic acid followed by 2-chloro-3-trifluoromethylbenzaldehyde (0.1 g, 0.51 mmol) and sodium triacetoxyborohydride (0.149, 0.68 mmol). After the resulting mixture was stirred at room temperature overnight water was added to quench the reaction. The aqueous layer was extracted with ethyl acetate. The combined organic layers was washed with brine, dried over sodium sulfate and concentrated in vacco. The crude mixture was purified by silica gel column chromatography using EtOAc:Hexane/25:75 as the eluent to give 50 mg (40% yield) of the title compound as an oil MS m/e 548.4 (M+H)+.

후처리

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacco
  8. customThe crude mixture was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-bc3d50e37c0643dda69ba45a1376ddda
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07365085B2

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