Sodium Carbonate → HCID 69102956、化合物

HRID 2220373ノート

反応式

HRID 2220373 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]([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]

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 24822808(3-(Cyclohexyloxy)-4-(methoxycarbonyl)phenyl)boronic acidHCID 86598946HCID 86598946、化合物

生成物 1

HCID 69102956HCID 69102956、化合物収率 83.1%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
75 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-71ea15d203c44d3b8e15117b07289541
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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