methyl (2R)-2-amino-5-[5-[{2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl}(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-4-pentynoate → methyl (2R)-5-[5-[{2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl}(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-3,4-dihydro-2H-pyrrole-2-carboxylate

HRID 69538

反応式

HRID 69538 の反応式
[NH2:1][C@H:2]([CH2:7][C:8]#[C:9][C:10]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[CH3:23])[C:13]([N:24]([C:26](=[O:44])[C:27]([C:30]2[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[C:32]([C:40]([F:43])([F:42])[F:41])[CH:31]=2)([CH3:29])[CH3:28])[CH3:25])=[CH:12][N:11]=1)[C:3]([O:5][CH3:6])=[O:4]>C(#N)C.FC(F)(F)S([O-])(=O)=O.[Ag+]>[F:37][C:36]([F:38])([F:39])[C:34]1[CH:35]=[C:30]([C:27]([CH3:28])([CH3:29])[C:26]([N:24]([CH3:25])[C:13]2[C:14]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=3[CH3:23])=[CH:15][C:10]([C:9]3[CH2:8][CH2:7][C@H:2]([C:3]([O:5][CH3:6])=[O:4])[N:1]=3)=[N:11][CH:12]=2)=[O:44])[CH:31]=[C:32]([C:40]([F:41])([F:43])[F:42])[CH:33]=1

参加物

4

反応物 1

HCID 57965568methyl (2R)-2-amino-5-[5-[{2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl}(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-4-pentynoate2 回

生成物 1

HCID 57965574methyl (2R)-5-[5-[{2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl}(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-3,4-dihydro-2H-pyrrole-2-carboxylate収率 118.8%

試薬・触媒・溶媒 2

HCID 76223Silver(I) trifluoromethanesulfonate触媒HCID 6342Acetonitrile溶媒

実験手順

Silver trifluoromethanesulfonate (0.381 g, 1.483 mmol) was added portionwise to a solution of methyl (2R)-2-amino-5-[5-[{2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl}(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-4-pentynoate (Intermediate 13, 1.85 g, 2.97 mmol) in anhydrous Acetonitrile (25 ml) and the resulting reaction mixture was stirred at room temperature overnight. Volatiles were evaporated under vacuo at room temperature. The residue was taken-up in dichloromethane and filtered through a plug of celite to afford 2.2 g of the title compound as a brown solid (the material contained some residual acetonitrile, therefore overall recovered amount was higher than the theoretical amount).

後処理

  1. customthe resulting reaction mixture
  2. customVolatiles were evaporated under vacuo at room temperature
  3. filtrationfiltered through a plug of celite

出典と根拠

ORDレコード
ord-0cb35fc63e4340b2ac368e0ac56b75f9
出典データセット
uspto-grants-2014_09
特許番号
US08822504B2

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