Toluene → Methyl 3-{[(4-nitrophenoxy)carbonyl]oxy}benzoate

HRID 1691714ノート

反応式

HRID 1691714 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl[C:13]([O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)=[O:14].C1(C)C=CC=CC=1>C(N(CC)CC)C>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([O:15][C:13]([O:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[O:14])=[CH:17][CH:18]=1)([O-:24])=[O:23]

参加物

5

反応物 3

HCID 1140TolueneHCID 821294-Nitrophenyl chloroformateHCID 88068Methyl 3-Hydroxybenzoate

生成物 1

HCID 66906106Methyl 3-{[(4-nitrophenoxy)carbonyl]oxy}benzoate収率 57.1%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

To a suspension of 5.000 g of methyl 3-hydroxybenzoate, 6.955 g of 4-nitrophenyl chloroformate, and 100 mL of toluene was added 4.81 mL of triethylamine at room temperature, followed by stirring overnight. The insolubles were removed by filtration, and as solvent was removed by distillation under reduced pressure to obtain 5.948 g of methyl 3-{[(4-nitrophenoxy)carbonyl]oxy}benzoate as a pale yellow solid. To a mixture of 100 mg of methyl 3-{[(4-nitrophenoxy)carbonyl]oxy}benzoate, 139 mg of tert-butyl {[3-(3-fluorophenyl)piperidin-4-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate, and 4 ml of THF was added 0.084 mL of triethylamine at room temperature, followed by stirring overnight. A saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 196 mg of 3-(methoxycarbonyl)phenyl 4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-(3-fluorophenyl)piperidine-1-carboxylate as a pale yellow oily compound.

後処理

  1. customThe insolubles were removed by filtration
  2. customas solvent was removed by distillation under reduced pressure

出典と根拠

ORDレコード
ord-c91e3159069b403180a69cb4ed1f24a3
出典データセット
uspto-grants-2012_04
特許番号
US08153658B2

反応ノート

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