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Cesium fluoride → (S)-2-[5-Naphthalen-1-yl-2-oxo-3-(4-trifluoromethylbenzoylamino)-2H-pyridin-1-yl]-3-phenylpropionic acid methyl ester

HRID 7807
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HRID 7807 반응식
[CH3:1][O:2][C:3](=[O:33])[C@@H:4]([N:12]1[CH:17]=[C:16](Br)[CH:15]=[C:14]([NH:19][C:20](=[O:31])[C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[C:13]1=[O:32])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.B(O)(O)[C:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[CH:37][CH:36]=1.[F-].[Cs+]>O1CCCC1.C(OCC)C.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:1][O:2][C:3](=[O:33])[C@@H:4]([N:12]1[CH:17]=[C:16]([C:43]2[C:44]3[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:40]=[CH:41][CH:42]=2)[CH:15]=[C:14]([NH:19][C:20](=[O:31])[C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[C:13]1=[O:32])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 25953Cesium fluorideHCID 2545321-Naphthaleneboronic acidHCID 69587645(S)-2-[5-Bromo-2-oxo-3-(4-trifluoromethylbenzoylamino)-2H-pyridin-1-yl]-3-phenylpropionic acid methyl ester

생성물 1

HCID 69587926(S)-2-[5-Naphthalen-1-yl-2-oxo-3-(4-trifluoromethylbenzoylamino)-2H-pyridin-1-yl]-3-phenylpropionic acid methyl ester수율 81%

시약·촉매·용매 3

HCID 178418851
HCID 178418851, 화합물
촉매
HCID 3283Diethyl Ether용매
HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of (S)-2-[5-bromo-2-oxo-3-(4-trifluoromethylbenzoylamino)-2H-pyridin-1-yl]-3-phenylpropionic acid methyl ester from Step E (66.8 mg, 0.128 mmol), 1-naphthyleneboronic acid (44.0 mg, 0.256 mmol), cesium fluoride (97 mg, 0.64 mmol), tris(dibenzylideneacetone)dipalladium(0) chloroform complex (13.0 mg, 0.013 mmol) and bis(tri-t-butylphosphine)palladium(0) (16.0 mg, 0.031 mmol) in tetrahydrofuran (2.0 mL) was heated to reflux for 15 h. The reaction mixture was cooled to room temperature, diluted with diethyl ether (100 mL), washed with saturated ammonium chloride solution and brine. The organic layer was separated, dried with sodium sulfate, filtered and concentrated. Purification by medium pressure liquid chromatography on silica gel (1:5 ethyl acetate/hexanes) gave 59 mg (81%) of the title compound as a semisolid. MS 571.2 (M+H)+.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 15 h
  3. washwashed with saturated ammonium chloride solution and brine
  4. customThe organic layer was separated
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by medium pressure liquid chromatography on silica gel (1:5 ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-0a77d0470a194567bea60da99ff1e7cf
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07087622B2

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