(p-Acetylphenoxy)acetic acid → 3-[2-(4-Acetyl-phenoxy)acetylamino]-benzoic acid methyl ester

HRID 1945377ノート

反応式

HRID 1945377 の反応式
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([OH:12])=O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:15][O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:15][O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:10](=[O:12])[CH2:9][O:8][C:7]2[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH3:2])=[CH:14][CH:13]=2)[CH:19]=1

参加物

6

反応物 4

HCID 74655(p-Acetylphenoxy)acetic acidHCID 757711-HydroxybenzotriazoleHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 81531Diisopropylethylamine

生成物 1

HCID 26213993-[2-(4-Acetyl-phenoxy)acetylamino]-benzoic acid methyl ester収率 97%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of the 4-acetylphenoxy acetic acid (97 mg, 0.5 mmol) and 3-amino benzoic acid methyl ester (113 mg, 0.75 mmol) in DMF (5.0 mL) were added EDCHCl (144 mg, 0.75 mmol), HOBT (101 mg, 0.75 mmol), and DIPEA (0.13 mL, 0.75 mmol). The reaction mixture was stirred at room temperature overnight, and then partitioned between Ethyl acetate and brine. The organic phase was dried (anhydrous MgSO4), and concentrated. Purification by silica gel column chromatography (n-Hexane:Ethyl acetate:MeOH=6:3:1) gave 3-[2-(4-acetyl-phenoxy)acetylamino]-benzoic acid methyl ester as a white solid (158 mg, 97% yield).

後処理

  1. custompartitioned between Ethyl acetate and brine
  2. dry with materialThe organic phase was dried (anhydrous MgSO4)
  3. concentrationconcentrated
  4. customPurification by silica gel column chromatography (n-Hexane:Ethyl acetate:MeOH=6:3:1)

出典と根拠

ORDレコード
ord-35dc122ed6444705805522cbf0e4f3a8
出典データセット
uspto-grants-2013_03
特許番号
US08394799B2

反応ノート

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