Methanol → 2'-Cyano-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acid

HRID 1845197ノート

反応式

HRID 1845197 の反応式
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])[CH:13]=[C:12]([C:23]([O:25]C)=[O:24])[CH:11]=1)#[N:2].[OH-].[Li+].CO>O>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])[CH:13]=[C:12]([C:23]([OH:25])=[O:24])[CH:11]=1)#[N:2]

参加物

5

反応物 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 58188323Methyl 2'-cyano-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylate

生成物 1

HCID 581881162'-Cyano-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A round-bottom flask was charged with methyl 2′-cyano-4′-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylate (0.17 g, 0.46 mmol), lithium hydroxide (17 mg, 0.70 mmol), methanol (5 mL), and water (1 mL). The mixture was stirred at room temperature overnight. The evolatiles were removed under reduced pressure and the residue was acidified with 1 N HCl, extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered, concentrated to afford the desired product as a white solid. LC-MS: 335.4 [M+1]+; 1H NMR (400 MHz, DMSO-d6): 8.14 (t, J=1.6 Hz, 1H), 8.10 (t, J=1.5 Hz, 1H), 7.93 (t, J=1.7 Hz, 1H), 7.83 (t, J=0.8 Hz, 1H), 7.66-7.60 (m, 2H), 3.51-3.42 (m, 4H), 2.42 (s, 3H), 1.91-1.83 (m, 4H).

後処理

  1. customThe evolatiles were removed under reduced pressure
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-d101ee3c4df64e3a92bce2b5592b8252
出典データセット
uspto-grants-2015_02
特許番号
US08946439B2

反応ノート

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