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

HRID 1357306ノート

反応式

HRID 1357306 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-66044f82a67b4094a48e2b8f8fdbfb30
出典データセット
uspto-grants-2003_07
特許番号
US06589970B2

反応ノート

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