Sodium Carbonate → HCID 69102956, 화합물

HRID 2220373노트

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HRID 2220373 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:18][C@@H:19]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[CH:33]1([O:39][C:40]2[CH:41]=[C:42](B(O)O)[CH:43]=[CH:44][C:45]=2[C:46]([O:48][CH3:49])=[O:47])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.O.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>[C:13]([O:12][C:11]([N:10]([CH2:18][C@@H:19]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)[CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:42]2[CH:43]=[CH:44][C:45]([C:46]([O:48][CH3:49])=[O:47])=[C:40]([O:39][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)[CH:41]=2)=[CH:3][CH:4]=1)=[O:17])([CH3:16])([CH3:15])[CH3:14]

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 24822808(3-(Cyclohexyloxy)-4-(methoxycarbonyl)phenyl)boronic acidHCID 86598946HCID 86598946, 화합물

생성물 1

HCID 69102956HCID 69102956, 화합물수율 83.1%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

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온도
75 °C

실험 절차

To a solution of tert-butyl [2-(4-bromophenyl)ethyl]-[(2R)-2-phenyl-2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-carbamate (620 mg) in 1,2-dimethoxyethane (7 ml) were added [3-(cyclohexyloxy)-4-(methoxycarbonyl)phenyl]boronic acid (410 mg), tetrakis(triphenylphosphine)palladium (99 mg) and aqueous solution of sodium carbonate (2M, 1.35 ml), and the mixture was stirred at 75° C. for 5 hours under nitrogen. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=9/1) to give methyl 4′-[2-[(tert-butoxycarbonyl)[(2R)-2-phenyl-2-(tetrahydro-2H-pyran-2-yloxy)ethyl]amino]ethyl]-3-(cyclohexyloxy)-4-biphenylcarboxylate (672 mg).

후처리

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=9/1)

출처 및 근거

ORD 기록
ord-71ea15d203c44d3b8e15117b07289541
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417060B2

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