Sodium Carbonate → HCID 69103505, 화합물

HRID 2220430노트

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HRID 2220430 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:18][C@H:19]([OH:26])[C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[CH2:27]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][C:36]=1[C:37]([O:39][CH3:40])=[O:38])[CH:28]([CH3:30])[CH3:29].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:13]([O:12][C:11]([N:10]([CH2:18][C@H:19]([OH:26])[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:33]2[CH:34]=[CH:35][C:36]([C:37]([O:39][CH3:40])=[O:38])=[C:31]([CH2:27][CH:28]([CH3:30])[CH3:29])[CH:32]=2)=[CH:3][CH:4]=1)=[O:17])([CH3:16])([CH3:15])[CH3:14]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 24822809HCID 24822809, 화합물HCID 67098073HCID 67098073, 화합물

생성물 1

HCID 69103505HCID 69103505, 화합물수율 62.5%

시약·촉매·용매 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

To a mixture of tert-butyl [2-(4-bromophenyl)ethyl]-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]carbamate (500 mg), [3-isobutyl-4-(methoxycarbonyl)phenyl]boronic acid (336 mg), [1,1′-bis(diphenylphosphino)feffocene]palladium(II) dichloride (48.5 mg) and 1,1′-bis(diphenylphosphino)ferrocene (16.4 mg) in N,N-dimethylformamide (3.75 ml) was added 2.0M aqueous sodium carbonate solution (2.08 ml) and the mixture was stirred at 90° C. for 3 hours. After cooling to room temperature, the mixture was partitioned between ethyl acetate (30 ml) and water (30 ml). The organic layer was separated, washed with brine (30 ml) and dried over magnesium sulfate. Filtration followed by evaporation under reduced pressure gave a crude product which was purified by column chromatography on silica gel (hexane/ethyl acetate=1/1 to 1/3) to give methyl 4′-[2-[[tert-butoxycarbonyl]-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]amino]ethyl]-3-isobutyl-4-biphenylcarboxylate (395 mg) as a yellow solid (foam).

후처리

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between ethyl acetate (30 ml) and water (30 ml)
  3. customThe organic layer was separated
  4. washwashed with brine (30 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration
  7. customfollowed by evaporation under reduced pressure
  8. customgave a crude product which
  9. customwas purified by column chromatography on silica gel (hexane/ethyl acetate=1/1 to 1/3)

출처 및 근거

ORD 기록
ord-effb71e5165f4623a43849138cdd0cb9
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417060B2

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