Triethylamine → (RS)-ethoxy-(2-oxo-3-phenylamino-2H-pyridin-1-yl)-acetic acid ethyl ester

HRID 1828096ノート

反応式

HRID 1828096 の反応式
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH2:17]([O:19][C:20](=[O:33])[CH:21]([N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH2:31])[C:26]1=[O:32])[O:22][CH2:23][CH3:24])[CH3:18].CC1(C)N([O])C(C)(C)CCC1>C(Cl)Cl>[CH2:17]([O:19][C:20](=[O:33])[CH:21]([O:22][CH2:23][CH3:24])[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:26]1=[O:32])[CH3:18]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 2724126TempoHCID 69641593(RS)-(3-amino-2-oxo-2H-pyridin-1-yl)-ethoxy-acetic acid ethyl ester

生成物 1

HCID 69641585(RS)-ethoxy-(2-oxo-3-phenylamino-2H-pyridin-1-yl)-acetic acid ethyl ester収率 47.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a 100 ml flask was added in sequence molecular sieves 4Å(200 mg), phenylboronic acid (418 mg), CH2Cl2 (10 ml), triethylamine (0.48 ml), a solution of (RS)-(3-amino-2-oxo-2H-pyridin-1-yl)-ethoxy-acetic acid ethyl ester (412 mg, example 19.2) in CH2Cl2 (10 ml), cupric acetate (31 mg) and TEMPO (295 mg). A CaCl2 trap was placed over the flask. The reaction was then stirred under air for 3 days. The solids were filtered off and washed with CH2Cl2. The filtrate was concentrated. The crude product was purified by chromatography (silica gel, gradient cyclohexane/EtOAc) to give (RS)-ethoxy-(2-oxo-3-phenylamino-2H-pyridin-1-yl)-acetic acid ethyl ester (258 mg) as green oil. MS 317.2 ([M+H]+)

後処理

  1. customA CaCl2 trap was placed over the flask
  2. filtrationThe solids were filtered off
  3. washwashed with CH2Cl2
  4. concentrationThe filtrate was concentrated
  5. customThe crude product was purified by chromatography (silica gel, gradient cyclohexane/EtOAc)

出典と根拠

ORDレコード
ord-7ae369e00fda4909827498ee2a511184
出典データセット
uspto-grants-2006_06
特許番号
US07056932B2

反応ノート

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