Methanol → Methyl 4-[2-(tert-butoxycarbonylamino)ethyl]benzoate

HRID 2305230ノート

反応式

HRID 2305230 の反応式
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:9][CH:8]=1)(=O)=O.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH3:61][OH:62].CN([CH:66]=[O:67])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:19]([O:18][C:16]([NH:15][CH2:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:61]([O:67][CH3:66])=[O:62])=[CH:8][CH:9]=1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

参加物

7

反応物 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 18459135trifluoro-methanesulfonic Acid 4-(2-tert-butoxycarbonylamino-ethyl)-phenyl Ester

生成物 1

HCID 22710013Methyl 4-[2-(tert-butoxycarbonylamino)ethyl]benzoate収率 76%

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

反応条件

温度
78 °C

実験手順

A mixture of 4-[2-(tert-butoxycarbonylamino)ethyl]-phenyl trifluoromethanesulfonate (6.11 g, 16.6 mmol), palladium(II) acetate (745 mg, 3.32 mmol), 1,3-bis-(diphenylphosphino)propane (1.37 g, 3.32 mmol), triethylamine (6.94 ml, 49.8 mmol), and MeOH (24ml) in DMF (60 ml) was purged for 30 min with carbon monoxide. The mixture was stirred under carbon monoxide atmosphere at 78° C. for 3 hours. After cooling the mixture to room temperature, the reaction mixture was diluted with EtOAc, washed with water, 1N-hydrochloric acid, water, saturated sodium hydrogencarbonate, water and brine successively, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:EtOAc, 4:1-3:1) to give methyl 4-[2-(tert-butoxycarbonylamino)ethyl]benzoate (3.52 g, 76%).

後処理

  1. customwas purged for 30 min with carbon monoxide
  2. temperatureAfter cooling the mixture to room temperature
  3. additionthe reaction mixture was diluted with EtOAc
  4. washwashed with water, 1N-hydrochloric acid, water, saturated sodium hydrogencarbonate, water and brine successively
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane:EtOAc, 4:1-3:1)

出典と根拠

ORDレコード
ord-c9eea0ea7072494e89b772851a645535
出典データセット
uspto-grants-2002_08
特許番号
US06437146B1

反応ノート

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