Sodium Carbonate → Methyl (s)-2-((tert-butoxycarbonyl)amino)-3-(4'-cyano-[1,1'-biphenyl]-4-yl)propanoate

HRID 708579ノート

反応式

HRID 708579 の反応式
[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1.[C:22]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)#[N:23].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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>[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:27]2[CH:28]=[CH:29][C:24]([C:22]#[N:23])=[CH:25][CH:26]=2)=[CH:8][CH:7]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 12967061(S)-Methyl 3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoate

生成物 1

HCID 66719271Methyl (s)-2-((tert-butoxycarbonyl)amino)-3-(4'-cyano-[1,1'-biphenyl]-4-yl)propanoate

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

Suzuki Coupling. To a solution of (S)-3-(4-Bromo-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester in toluene (250 mL) was added 4-cyanobenzeneboronic acid, Pd(PPh3)4, and 1N Na2CO3 solution (105 mL). The mixture was heated at reflux for 7 h. After completion of the reaction, the aqueous layer was drained. The organic layer was washed with 10% Na2CO3 and 1 N HCl. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford the crude product. The residue was then purified by column chromatography (hexanes-EtOAc) to provide (S)-2-tert-Butoxycarbonylamino-3-(4′-cyano-biphenyl-4-yl)-propionic acid methyl ester (18.2 g). LCMS (m/z) 382.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 7 h
  3. customAfter completion of the reaction
  4. washThe organic layer was washed with 10% Na2CO3 and 1 N HCl
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto afford the crude product
  8. customThe residue was then purified by column chromatography (hexanes-EtOAc)

出典と根拠

ORDレコード
ord-8fd0e14092b1453e82257d14796fecff
出典データセット
uspto-grants-2015_11
特許番号
US09175003B2

反応ノート

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