Water → {4-[(E)-2-(2-chloro-6-methoxy-phenyl)-vinyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester

HRID 1051226ノート

反応式

HRID 1051226 の反応式
[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([C:17]2[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:25])O)=[C:10]([N+:26]([O-:28])=[O:27])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>C1COCC1>[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:17]2[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:25])=[C:10]([N+:26]([O-:28])=[O:27])[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 90103009{4-[2-(2-Chloro-6-methoxy-phenyl)-2-hydroxy-ethyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester

生成物 1

HCID 90102327{4-[(E)-2-(2-chloro-6-methoxy-phenyl)-vinyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester収率 60%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

To a solution of {4-[2-(2-chloro-6-methoxy-phenyl)-2-hydroxy-ethyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester (0.45 g, 1.06 mmol)in THF (10 mL) was added 2,2,2-trifluoroacetic anhydride (671 mg, 3.18 mmol) at 25° C. resulting in a color change to dark blue. The reaction was allowed to stir at 25° C. for 30 min after which 8-diazabicyclo[5.4.0]undec-7-ene (0.76 g, 5.00 mmol) was added. The reaction was heated to 70° C. for 3 h and then cooled to 25° C. and poured into water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave a brown solid. Flash chromatography (90/10 hexanes/ethyl acetate) afforded {4-[(E)-2-(2-chloro-6-methoxy-phenyl)-vinyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester (240 mg, 60%) as an oil.

後処理

  1. customresulting in a color change to dark blue
  2. additionwas added
  3. temperaturecooled to 25° C.
  4. extractionThe aqueous phase was extracted three times with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationFiltration
  8. concentrationfollowed by concentration in vacuo
  9. customgave a brown solid

出典と根拠

ORDレコード
ord-915310cc52254c31a41c60e1eb95dbdb
出典データセット
uspto-grants-2016_07
特許番号
US09388166B2

反応ノート

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