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

HRID 1942587ノート

反応式

HRID 1942587 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[CH2:33]C(CC(OC)=O)[CH2:31]1.[C:39]([O-:42])(=[O:41])[CH3:40].[Na+].[CH3:44]C(O)=O>CO>[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:27])([F:29])[F:28])[CH:17]=3)=[N:14][N:15]=2)=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][N:30]1[CH2:33][CH:40]([C:39]([O:42][CH3:44])=[O:41])[CH2:31]1)[CH3:2]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 53408531Methyl (azetidin-3-yl)acetateHCID 866589982-Ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}benzaldehyde

生成物 1

HCID 66981848Methyl 1-[(2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)methyl]-3-azetidinecarboxylate

試薬・触媒・溶媒 1

HCID 887Methanol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) (52 mg) and methyl 3-azetidinylacetate (109 mg) in methanol (10.00 mL) stirred at room temperature was added sodium acetate (55 mg) and AcOH (0.035 mL). The reaction mixture was stirred at room temperature for 10 min. After that, the solvent was removed by evaporation. The residue was dissolved in dichloromethane (DCM) (10 mL), sodium triacetoxyborohydride (79 mg) was added. 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 solution was washed by brine, dried over anhydrous Na2SO4. The dried solution was filtered and concentrated to afford methyl 1-[(2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)methyl]-3-azetidinecarboxylate (D8) (64.3 mg), which was used for the next without further purification. MS (ES): C26H28F3N3O3S requires 519. found 520.2 (M+H+).

後処理

  1. customAfter that, the solvent was removed by evaporation
  2. dissolutionThe residue was dissolved in dichloromethane (DCM) (10 mL)
  3. additionsodium triacetoxyborohydride (79 mg) was added
  4. stirringStirring
  5. waitcontinued for 2 h
  6. additionWater was added
  7. customto quench
  8. customthe reaction, and DCM
  9. customwas removed by evaporation
  10. extractionThe mixture was extracted by EA for 3 times
  11. washThe combined organic solution was washed by brine
  12. dry with materialdried over anhydrous Na2SO4
  13. filtrationThe dried solution was filtered
  14. concentrationconcentrated

出典と根拠

ORDレコード
ord-728bee0a748e4a7cb45f59fb7866db88
出典データセット
uspto-grants-2013_03
特許番号
US08389508B2

反応ノート

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