Hydrochloric Acid → [5-(5-{4-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl}-1,3,4-thiadiazol-2-yl)-2H-tetrazol-2-yl]acetic acid

HRID 561195ノート

反応式

HRID 561195 の反応式
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:31]=[CH:30][CH:29]=[CH:28][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[S:16][C:15]([C:17]3[N:18]=[N:19][N:20]([CH2:22][C:23]([O:25]CC)=[O:24])[N:21]=3)=[N:14][N:13]=2)[CH2:8][CH2:7]1.[OH-].[Na+].Cl>C1COCC1.CO>[F:33][C:2]([F:1])([F:32])[C:3]1[CH:31]=[CH:30][CH:29]=[CH:28][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[S:16][C:15]([C:17]3[N:18]=[N:19][N:20]([CH2:22][C:23]([OH:25])=[O:24])[N:21]=3)=[N:14][N:13]=2)[CH2:8][CH2:7]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86620455ethyl [5-(5-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-1,3,4-thiadiazol-2-yl)-2H-tetrazol-2-yl]acetate

生成物 1

HCID 57518492[5-(5-{4-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl}-1,3,4-thiadiazol-2-yl)-2H-tetrazol-2-yl]acetic acid

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

A solution of ethyl [5-(5-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-1,3,4-thiadiazol-2-yl)-2H-tetrazol-2-yl]acetate (134 mg, 0.28 mmol) in THF/MeOH (2:1) (v/v) (4.6 mL) was treated with aqueous 1 N NaOH (1.5 mL). The reaction mixture was stirred at room temperature until TLC indicated disappearance of the starting material. The reaction mixture was poured into aqueous aqueous 0.5 N HCl, extracted with EtOAc, washed with brine. The organic layer was dried (Na2SO4) and filtered. Evaporation of the solvent was followed by trituration in a mixture of Et2O/heptane with stirring for 1 h at room temperature. After this time, the title compound was collected by filtration as a white solid.

後処理

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customEvaporation of the solvent
  6. additionwas followed by trituration in a mixture of Et2O/heptane
  7. stirringwith stirring for 1 h at room temperature
  8. filtrationAfter this time, the title compound was collected by filtration as a white solid

出典と根拠

ORDレコード
ord-f5830db75438493ea0f01ea103a4ec60
出典データセット
uspto-grants-2011_11
特許番号
US08063224B2

反応ノート

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