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

HRID 561195노트

반응식

HRID 561195 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f5830db75438493ea0f01ea103a4ec60
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063224B2

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