Citric Acid → Tert-butyl 4-(4-((tert-butoxycarbonyl)(methyl)amino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate

HRID 454768

反応式

HRID 454768 の反応式
C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][N:8]([C:16]1[CH:21]=[CH:20][C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18][CH:17]=1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].Br[C:32]1[CH:44]=[CH:43][C:35]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[C:34]([NH:45][C:46]([C:48]2[CH:49]=[N:50][CH:51]=[C:52]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[CH:53]=2)=[O:47])[CH:33]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C.COCCOC.O>[C:11]([O:10][C:9]([N:8]([CH3:7])[C:16]1[CH:17]=[CH:18][C:19]([C:32]2[CH:44]=[CH:43][C:35]([C:36]([O:38][C:39]([CH3:41])([CH3:40])[CH3:42])=[O:37])=[C:34]([NH:45][C:46]([C:48]3[CH:49]=[N:50][CH:51]=[C:52]([C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)[CH:53]=3)=[O:47])[CH:33]=2)=[CH:20][CH:21]=1)=[O:15])([CH3:12])([CH3:13])[CH3:14]

参加物

9

反応物 4

HCID 311Citric AcidHCID 10340Sodium CarbonateHCID 4712653tert-Butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamateHCID 58508430Tert-butyl 4-bromo-2-(5-phenylpyridine-3-carboxamido)benzoate

生成物 1

HCID 66990300Tert-butyl 4-(4-((tert-butoxycarbonyl)(methyl)amino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate収率 83.4%

試薬・触媒・溶媒 4

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Water (0.60 mL), sodium carbonate (88 mg), tert-butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (0.13 g), and bis(triphenylphosphine)palladium(II) dichloride (5.0 mg) were added to an ethylene glycol dimethyl ether (2.0 mL) solution of tert-butyl 4-bromo-2-(5-phenylpyridine-3-carboxamido)benzoate (0.15 g), followed by heating to reflux under a nitrogen atmosphere for 1 hour. The reaction mixture was cooled to room temperature, and then a 10% aqueous solution of citric acid and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate] to obtain 0.16 g of tert-butyl 4-(4-((tert-butoxycarbonyl)(methyl)amino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate as a white solid.

後処理

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 1 hour
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate]

出典と根拠

ORDレコード
ord-66c81f6e2ef04674afc77253705b5802
出典データセット
uspto-grants-2013_07
特許番号
US08492582B2

関連ノート

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