Hydrochloric Acid → HCID 59432457, 화합물

HRID 2353948노트

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HRID 2353948 반응식
COC(=O)[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([CH3:11])[C:5]=1[N:12]([CH2:19][CH2:20][CH2:21][C:22]([O:24]CC)=O)[C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14].CC(C)([O-])C.[K+].Cl.[Cl-].[Li+]>C1COCC1.[Cl-].[Na+].O>[CH:16]([O:15][C:13]([N:12]1[CH2:19][CH2:20][CH2:21][C:22](=[O:24])[C:4]2[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([CH3:11])[C:5]1=2)=[O:14])([CH3:17])[CH3:18]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 23665647Potassium tert-butoxideHCID 68681230HCID 68681230, 화합물

생성물 1

HCID 59432457HCID 59432457, 화합물수율 75.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 57417360Sodium chloride; water용매

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온도
160 °C

실험 절차

Add a solution of 2-[(3-Ethoxycarbonyl-propyl)-isopropoxycarbonyl-amino]-4-bromo-3-methyl-benzoic acid methyl ester (3.47 g, 7.81 mmol) in THF (120 mL) to a solution of potassium tert-butoxide (15.6 mL, 15.62 mmol, 1 M in THF) in THF (120 mL) at room temperature under an atmosphere of nitrogen. After 2 h, pour the mixture into ice/water. Treat aqueous phase with 1M HCl to pH neutral and extract with dichloromethane. Dry the organic layer over anhydrous magnesium sulfate, filter, and remove the solvent under reduced pressure. Dissolve the former crude in DMSO (66 mL) and add water (4 drops) followed by addition of lithium chloride (0.882 g, 20.8 mmol) and heat the resulting solution at 160° C. for 2 h. Cool the mixture to room temperature and pour into brine. Extract the mixture with ethyl acetate. Dry the organic layers over anhydrous magnesium sulfate, filter and remove the solvent under reduced pressure. Purify the residue by flash chromatography, eluting with hexanes/ethyl acetate, to afford the title compound (2.0 g, 72% over two steps): MS (ES+): 341 (M+H).

후처리

  1. extractionextract with dichloromethane
  2. dry with materialDry the organic layer over anhydrous magnesium sulfate
  3. filtrationfilter
  4. customremove the solvent under reduced pressure
  5. dissolutionDissolve the former crude in DMSO (66 mL)
  6. additionadd water (4 drops)
  7. temperatureCool the mixture to room temperature
  8. extractionExtract the mixture with ethyl acetate
  9. dry with materialDry the organic layers over anhydrous magnesium sulfate
  10. filtrationfilter
  11. customremove the solvent under reduced pressure
  12. customPurify the residue by flash chromatography
  13. washeluting with hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-2023753102d1406da7e058c2b614f6ce
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07749992B2

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