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Potassium Carbonate → 6-(4-{[3-(2,6-Dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}phenyl)-2-naphthoic acid

HRID 646025
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HRID 646025 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([C:18]([O:20]C)=[O:19])[CH:12]=[CH:11]3)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:29][C:30]1[C:31]([C:38]2[C:43]([Cl:44])=[CH:42][CH:41]=[CH:40][C:39]=2[Cl:45])=[N:32][O:33][C:34]=1[CH:35]([CH3:37])[CH3:36].[OH-].[Na+]>CN(C=O)C.CCOC(C)=O.O.C1COCC1.CCO>[Cl:44][C:43]1[CH:42]=[CH:41][CH:40]=[C:39]([Cl:45])[C:38]=1[C:31]1[C:30]([CH2:29][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:17]=[C:16]4[C:15](=[CH:10][CH:9]=3)[CH:14]=[C:13]([C:18]([OH:20])=[O:19])[CH:12]=[CH:11]4)=[CH:4][CH:3]=2)=[C:34]([CH:35]([CH3:37])[CH3:36])[O:33][N:32]=1
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참가 물질

10

반응물 4

HCID 11430Potassium Carbonate2회HCID 14798Sodium HydroxideHCID 19834505Methyl 6-(4-hydroxyphenyl)-2-naphthoateHCID 592648754-(Chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazole2회

생성물 1

HCID 247391706-(4-{[3-(2,6-Dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}phenyl)-2-naphthoic acid수율 94%

시약·촉매·용매 5

HCID 702Ethanol용매HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To solution of methyl 6-(4-hydroxyphenyl)-2-naphthoate (55 mg, 0.20 mmol) in DMF (1.0 mL) was added K2CO3 (68 mg, 0.49 mmol) and 4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazole (91 mg, 0.30 mmol) and the mixture was stirred at ambient temperature for 12 hr. Additional 4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazole (50 mg, 0.16 mmol) and K2CO3 (68 mg, 0.49 mmol) in DMF (0.5 mL) was added and the mixture stirred at 70° C. for 3 hr. The solution was diluted with 50 mL EtOAc then washed with three 25 mL portions of H2O followed by 25 mL of brine then dried over Na2SO4, filtered, concentrated, and purified by silica gel chromatography (12 g of silica gel eluting with 0-40% EtOAc in hexanes over 45 minutes.) Product fractions were pooled and concentrated. To this residue was added EtOH (2.5 mL), THF (1.0 mL), H2O (0.5 mL) and NaOH (35 mg, 0.84 mmol) and the solution was stirred at 60° C. for 12 hr. The solution was concentrated to ˜⅓ volume then added dropwise to 1.0 N HCl (6 mL, aq.) The resulting solids were collected by suction filtration, washed with H2O and dried to give the title compound as an off-white solid (42 mg, 94%.) 1H NMR (DMSO-d6): δ 13.0 (broad s, 1H), 8.57 (s, 1H), 8.18 (s, 1H), 8.12 (d, J=9 Hz, 1H), 8.01 (d, J=9 Hz, 1H), 7.95 (d, J=9 Hz, 1H), 7.85 (d, J=9 Hz, 1H), 7.69 (d, J=8 Hz, 2H), 7.62 (d, J=8 Hz, 2H), 7.59-7.51 (m, 1H), 6.91 (d, J=8 Hz, 2H), 4.87 (s, 2 H), 3.45 (septet, J=7 Hz, 1H), 1.33 (d, J=7 Hz, 6H). ESI-LCMS m/z 532 (M+H)+.

후처리

  1. stirringthe mixture stirred at 70° C. for 3 hr
  2. washthen washed with three 25 mL portions of H2O
  3. dry with materialthen dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (12 g of silica gel eluting with 0-40% EtOAc in hexanes over 45 minutes.) Product fractions
  7. concentrationconcentrated
  8. stirringthe solution was stirred at 60° C. for 12 hr
  9. concentrationThe solution was concentrated
  10. additionthen added dropwise to 1.0 N HCl (6 mL, aq.) The resulting solids
  11. filtrationwere collected by suction filtration
  12. washwashed with H2O
  13. customdried

출처 및 근거

ORD 기록
ord-1b97e3eebbb94e1c8fb1e49d6647c92b
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07705028B2

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