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Acetic Acid → Ethyl 1-[(2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)methyl]-4-piperidinecarboxylate

HRID 1942586
ノート
印刷プレビュー

反応式

HRID 1942586 の反応式
[CH2:1]([C:3]1[C:10]([C:11]2[S:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=3)=[N:14][N:15]=2)=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O)[CH3:2].[NH:30]1[CH2:35][CH2:34][CH:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:32][CH2:31]1.CC(O)=O>C(O)C>[CH2:1]([C:3]1[C:10]([C:11]2[S:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:24])[CH3:25])=[C:18]([C:26]([F:28])([F:29])[F:27])[CH:17]=3)=[N:14][N:15]=2)=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][N:30]1[CH2:35][CH2:34][CH:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:32][CH2:31]1)[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 176Acetic AcidHCID 70770Ethyl 4-piperidinecarboxylateHCID 866589982-Ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}benzaldehyde

生成物 1

HCID 66981714Ethyl 1-[(2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)methyl]-4-piperidinecarboxylate収率 99.9%

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒

実験手順

To a solution of 2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}benzaldehyde (D6) (54 mg) and ethyl 4-piperidinecarboxylate (101 mg) in ethanol (10 mL) stirred at room temperature was added AcOH (0.037 mL). The reaction mixture was stirred at room temperature for 10 min. Then the solvent was removed by evaporation. To the residue was added dichloromethane (DCM) (10 mL) and sodium triacetoxyborohydride (82 mg). Stirring continued for 2 h. Water was added to quench the reaction, and DCM was removed by evaporation. The mixture was extracted by EA for 3 times. The combined organic phases were washed by brine, dried over anhydrous Na2SO4. The dried solution was filtered and concentrated to afford the crude product ethyl 1-[(2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)methyl]-4-piperidinecarboxylate (D7) (72.1 mg). MS (ES): C29H34F3N3O3S requires 561. found 562.1 (M+H+).

後処理

  1. customThen the solvent was removed by evaporation
  2. additionTo the residue was added dichloromethane (DCM) (10 mL) and sodium triacetoxyborohydride (82 mg)
  3. stirringStirring
  4. waitcontinued for 2 h
  5. additionWater was added
  6. customto quench
  7. customthe reaction, and DCM
  8. customwas removed by evaporation
  9. extractionThe mixture was extracted by EA for 3 times
  10. washThe combined organic phases were washed by brine
  11. dry with materialdried over anhydrous Na2SO4
  12. filtrationThe dried solution was filtered
  13. concentrationconcentrated

出典と根拠

ORDレコード
ord-25e379eb5b8e45f18daed6c728ff9488
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08389508B2

反応ノート

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