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

HRID 39060노트

반응식

HRID 39060 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 66719271Methyl (s)-2-((tert-butoxycarbonyl)amino)-3-(4'-cyano-[1,1'-biphenyl]-4-yl)propanoate수율 68.2%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

Suzuki coupling: To a solution of (S)-3-(4-Bromo-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester (70.1 mmol) in toluene (250 mL) was added 4-cyanobenzeneboronic acid (105 mmol), Pd(PPh3)4 (3.5 mmol), 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 was washed with 10% Na2CO3 and 1 N HCl. The organic was dried over sodium sulfate and concentrated under reduced pressure to afford the crude product. The residue was 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). LC-MS (m/z) 382.

후처리

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

출처 및 근거

ORD 기록
ord-cdee7bbac04b46c2b7ccfc5ab6dbad03
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524708B2

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