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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
ノート
印刷プレビュー

反応式

HRID 7807 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418851
HCID 178418851、化合物
触媒
HCID 3283Diethyl Ether溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-0a77d0470a194567bea60da99ff1e7cf
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07087622B2

反応ノート

読み込み中…

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