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

HRID 1945377노트

반응식

HRID 1945377 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-35dc122ed6444705805522cbf0e4f3a8
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394799B2

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