Sodium Carbonate → HCID 69103505、化合物

HRID 2220430ノート

反応式

HRID 2220430 の反応式
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]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 24822809HCID 24822809、化合物HCID 67098073HCID 67098073、化合物

生成物 1

HCID 69103505HCID 69103505、化合物収率 62.5%

試薬・触媒・溶媒 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-effb71e5165f4623a43849138cdd0cb9
出典データセット
uspto-grants-2008_08
特許番号
US07417060B2

反応ノート

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