Water → methyl (S)-2-propyloxy-3-[3'-(methylamino)biphenyl-4-yl]propanoate

HRID 1865449ノート

反応式

HRID 1865449 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([O:14][CH2:15][CH2:16][CH3:17])[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH3:18][NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:21]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:15]([O:14][C@@H:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([NH:19][CH3:18])[CH:21]=2)=[CH:3][CH:4]=1)[C:10]([O:12][CH3:13])=[O:11])[CH2:16][CH3:17]

参加物

7

反応物 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 57976762N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 67305005methyl (S)-3-(4-bromophenyl)-2-(propyloxy)propanoate

生成物 1

HCID 67305428methyl (S)-2-propyloxy-3-[3'-(methylamino)biphenyl-4-yl]propanoate収率 70.3%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

38 mg (0.033 mmol) of tetrakis(triphenylphosphine)palladium are added to a solution of 100 mg (0.33 mmol) of methyl (S)-3-(4-bromophenyl)-2-(propyloxy)propionate and 90 mg (0.39 mmol) of methyl[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine in 1 ml of dimethylformamide. 0.2 ml of a 2M potassium phosphate solution is added and the reaction mixture is stirred at 90° C. for 2 hours. The reaction is halted by the addition of 10 ml of water and then extraction is carried out with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated and then the residue is chromatographed on silica gel (heptane/ethyl acetate 80/20). 76 mg of methyl (S)-2-propyloxy-3-[3′-(methylamino)biphenyl-4-yl]propanoate are obtained in the form of an oil. Yield=70%.

後処理

  1. extractionextraction
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated
  4. customthe residue is chromatographed on silica gel (heptane/ethyl acetate 80/20)

出典と根拠

ORDレコード
ord-fdddbb17d11847068ff2573a8ab7ed49
出典データセット
uspto-grants-2009_12
特許番号
US07626054B2

反応ノート

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