Sodium Carbonate → HCID 69102258、化合物

HRID 2220427ノート

反応式

HRID 2220427 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH2:19][C@H:20]([OH:27])[C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1.[CH2:28]([O:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][C:38]=1[C:39]([O:41][CH3:42])=[O:40])[CH:29]([CH3:31])[CH3:30].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].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:14]([O:13][C:12]([N:11]([CH2:19][C@H:20]([OH:27])[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[CH2:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:35]2[CH:36]=[CH:37][C:38]([C:39]([O:41][CH3:42])=[O:40])=[C:33]([O:32][CH2:28][CH:29]([CH3:31])[CH3:30])[CH:34]=2)=[CH:3][CH:4]=1)=[O:18])([CH3:17])([CH3:16])[CH3:15]

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 24824482HCID 24824482、化合物HCID 86598957HCID 86598957、化合物

生成物 1

HCID 69102258HCID 69102258、化合物収率 92.7%

試薬・触媒・溶媒 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a mixture of tert-butyl [3-(4-bromophenyl)propyl]-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]carbamate (312 mg), [3-isobutoxy-4-(methoxycarbonyl)phenyl]boronic acid (207 mg), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (58.4 mg) and 1,1′-bis(diphenylphosphino)ferrocene (7.93 mg) in N,N-dimethylformamide (3.12 ml) was added 2.0M aqueous sodium carbonate solution (1.25 ml) and the mixture was stirred at 90° C. for 2.5 hours. After cooling to room temperature, palladium was removed by filtration through a Celite cake. The mixture was extracted with ethyl acetate and the extract was washed with water and brine 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 give methyl 4′-[3-[(tert-butoxycarbonyl)[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]amino]-propyl]-3-isobutoxy-4-biphenylcarboxylate (374 mg) as a yellow solid (foam).

後処理

  1. temperatureAfter cooling to room temperature
  2. custompalladium was removed by filtration through a Celite cake
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed with water and brine
  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)

出典と根拠

ORDレコード
ord-13c2b630dba9448194dc35feeca2feb5
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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