Hydrochloric Acid → 4-(3-((5-Cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)-3-fluorobenzoic acid

HRID 1748217노트

반응식

HRID 1748217 반응식
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][C:16]([F:19])([F:18])[F:17])[C:5]=2[CH2:20][O:21][CH:22]2[CH2:28][CH:27]3[N:29]([C:30]4[CH:39]=[CH:38][C:33]([C:34]([O:36]C)=[O:35])=[CH:32][C:31]=4[F:40])[CH:24]([CH2:25][CH2:26]3)[CH2:23]2)[CH2:3][CH2:2]1.CO.[OH-].[K+].Cl>O1CCCC1.C(OCC)(=O)C>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][C:16]([F:18])([F:17])[F:19])[C:5]=2[CH2:20][O:21][CH:22]2[CH2:23][CH:24]3[N:29]([C:30]4[CH:39]=[CH:38][C:33]([C:34]([OH:36])=[O:35])=[CH:32][C:31]=4[F:40])[CH:27]([CH2:26][CH2:25]3)[CH2:28]2)[CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 67983240HCID 67983240, 화합물

생성물 1

HCID 679850254-(3-((5-Cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)-3-fluorobenzoic acid

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

The ester above, methyl 4-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)-3-fluorobenzoate (24 mg, 0.043 mmoles) was dissolved in tetrahydrofuran (0.5 mL) and methanol (0.5 mL) and subjected to an aqueous solution of potassium hydroxide (6 N aqueous solution, 0.5 mL, 3.0 mmoles). The mixture was heated to 70° C. for 2 hours and then cooled to RT. The pH of the solution was adjusted to 6 using aqueous HCl (0.5 mL of 6N). The mixture was diluted with ethyl acetate (20 mL), extracted and water washed (3×1 mL). The organics were dried (MgSO4) then evaporated in vacuo. The product crystallized upon concentration of the ethyl acetate mother liquor, was washed with sparing ice cold ethyl acetate (0.5 mL), and the white solid dried to give the title compound.

후처리

  1. temperaturecooled to RT
  2. extractionextracted
  3. washwater washed (3×1 mL)
  4. dry with materialThe organics were dried (MgSO4)
  5. customthen evaporated in vacuo
  6. customThe product crystallized upon concentration of the ethyl acetate mother liquor
  7. washwas washed with sparing ice cold ethyl acetate (0.5 mL)
  8. customthe white solid dried

출처 및 근거

ORD 기록
ord-ed33e7ec382c4564a15c6a9cd32dfbcc
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150568B2

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