Sodium Carbonate → HCID 69102258, 화합물

HRID 2220427노트

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HRID 2220427 반응식
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]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 24824482HCID 24824482, 화합물HCID 86598957HCID 86598957, 화합물

생성물 1

HCID 69102258HCID 69102258, 화합물수율 92.7%

시약·촉매·용매 3

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

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온도
90 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-13c2b630dba9448194dc35feeca2feb5
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417060B2

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