Cesium carbonate → 2-(1-Bromo-6-{[(4-cyclohexyl-benzoyl)-methyl-amino]-methyl}-naphthalen-2-yloxy)-3-phenyl-propionic acid methyl ester

HRID 1357306노트

반응식

HRID 1357306 반응식
[Br:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:13][N:14]([CH3:29])[C:15](=[O:28])[C:16]1[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=1)=[CH:7]2.[CH3:30][O:31][C:32](=[O:49])[CH:33](OS(C(F)(F)F)(=O)=O)[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:30][O:31][C:32](=[O:49])[CH:33]([O:12][C:11]1[CH:10]=[CH:9][C:8]2[C:3](=[CH:4][CH:5]=[C:6]([CH2:13][N:14]([C:15](=[O:28])[C:16]3[CH:17]=[CH:18][C:19]([CH:22]4[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]4)=[CH:20][CH:21]=3)[CH3:29])[CH:7]=2)[C:2]=1[Br:1])[CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 13388932alpha-(Trifluoromethylsulfonyloxy)hydrocinnamic acid methyl esterHCID 18505343N-(5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-4-cyclohexyl-N-methyl-benzamide

생성물 1

HCID 691377602-(1-Bromo-6-{[(4-cyclohexyl-benzoyl)-methyl-amino]-methyl}-naphthalen-2-yloxy)-3-phenyl-propionic acid methyl ester수율 48%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of N-(5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-4-cyclohexyl-N-methyl-benzamide (799 mg, 1.51 mmol), prepared in the previous step, 3-phenyl-2-trifluoromethanesulfonyloxypropionic acid methyl ester (1.66 mmol), prepared in step 2 of Example 7, and cesium carbonate (985 mg, 3.0 mmol) in acetone was stirred at room temperature for 3 h. The reaction was partitioned between water and ethyl acetate. The aqueous layer was separated and extracted three times with ethyl acetate. The combined extracts were dried (Na2SO4) and the solvent removed under reduced pressure. Purification of the residue by column chromatography using 10%-20% ethyl acetate-hexanes as the eluent gave 2-(1-bromo-6-{[(4-cyclohexyl-benzoyl)-methyl-amino]-methyl}-naphthalen-2-yloxy)-3-phenyl-propionic acid methyl ester (445 mg, 48%), LCMS ES+(Calc'd: 613.2; Found: 614.3).

후처리

  1. customThe reaction was partitioned between water and ethyl acetate
  2. customThe aqueous layer was separated
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. customthe solvent removed under reduced pressure
  6. customPurification of the residue by column chromatography

출처 및 근거

ORD 기록
ord-66044f82a67b4094a48e2b8f8fdbfb30
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06589970B2

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