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Sodium Hydroxide → (2-(3-Methoxy-propyl)-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid

HRID 1393100
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HRID 1393100 반응식
C([O:3][C:4](=[O:37])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:31])[CH2:14][C:15]2[S:19][C:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[N:17][C:16]=2[CH3:30])=[CH:9][C:8]=1[CH2:32][CH2:33][CH2:34][O:35][CH3:36])C.[OH-].[Na+]>C1COCC1.CCO>[CH3:36][O:35][CH2:34][CH2:33][CH2:32][C:8]1[CH:9]=[C:10]([N:13]([CH3:31])[CH2:14][C:15]2[S:19][C:18]([C:20]3[CH:21]=[CH:22][C:23]([C:26]([F:28])([F:29])[F:27])=[CH:24][CH:25]=3)=[N:17][C:16]=2[CH3:30])[CH:11]=[CH:12][C:7]=1[O:6][CH2:5][C:4]([OH:37])=[O:3]
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반응물 2

HCID 14798Sodium HydroxideHCID 69220724(2-(3-Methoxy-propyl)-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester

생성물 1

HCID 11477701(2-(3-Methoxy-propyl)-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid

시약·촉매·용매 1

HCID 21873804Tetrahydrofuran ethanol용매

실험 절차

0.280 g (0.52 mmol) of the above prepared (2-(3-methoxy-propyl)-4-{methyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenoxy)-acetic acid ethyl ester was dissolved in 3.3 ml of THF/EtOH=1/1, treated with 1.56 ml (3 eq.) of 1N NaOH, and kept at ambient temperature for 0.5 h. The reaction mixture was then poured onto crashed ice/HCl dil., extracted twice with EtOAc, the organic layer washed with water and brine, dried over sodium sulfate, and evaporated to dryness. Crystallization from hexane/EtOAc afforded finally 0.209 g of the title compound as off-white crystals of mp. 142-143° C., MS: 507.5 (M-H)−.

후처리

  1. additionThe reaction mixture was then poured
  2. extractionextracted twice with EtOAc
  3. washthe organic layer washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customCrystallization from hexane/EtOAc

출처 및 근거

ORD 기록
ord-faefa4b1870a4f169d3fc246c4e39ba6
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07345067B2

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