Triethylamine → Acetic acid (4-methoxy-phenyl)-(3-methyl-isoxazol-5-ylcarbamoyl)-methyl ester

HRID 1272067

反応式

HRID 1272067 の反応式
[C:1]([O:4][CH:5]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[C:6]([OH:8])=O)(=[O:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[NH2:23][C:24]1[O:28][N:27]=[C:26]([CH3:29])[CH:25]=1.CCN(CC)CC>C(Cl)Cl.CN(C=O)C>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH:5]([O:4][C:1](=[O:3])[CH3:2])[C:6](=[O:8])[NH:23][C:24]2[O:28][N:27]=[C:26]([CH3:29])[CH:25]=2)=[CH:10][CH:11]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 845905-Amino-3-methylisoxazoleHCID 18456650Acetoxy-(4-methoxy-phenyl)-acetic acid

生成物 1

HCID 58847459Acetic acid (4-methoxy-phenyl)-(3-methyl-isoxazol-5-ylcarbamoyl)-methyl ester収率 71.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of acetoxy-(4-methoxy-phenyl)-acetic acid (79a) (2.78 g, 12.40 mmol) in CH2Cl2 (50 mL), was added 2.0 M oxalyl chloride in CH2Cl2 (9.30 mL, 18.60 mmol), followed by 10 drops of DMF. The mixture was stirred at ambient temperature for one hour, concentrated and further dried under high vacuum. It was re-dissolved in CH2Cl2 (50 mL); to this solution was added 5-amino-3-methylisoxazole (1.34 g, 13.66 mmol), followed by Et3N (2.60 mL, 18.60 mmol). After stirring at ambient temperature overnight, the mixture was concentrated in vacuo and purified by flash column chromatography eluting with 1:1 EtOAc and hexanes to provide 2.70 g yellow solid as the intermediate 79b. 1H NMR (300 MHz, CDCl3) δ 8.56 (s, 1H), 7.36 (d, 2H, J=8.67 Hz), 6.90 (d, 2H, J=8.67 Hz), 6.24 (s, 1H), 6.17 (s, 1H), 3.80 (s, 3H), 2.25 (s, 3H), 2.22 (s, 3H). LCMS (ESI—) [M−H]/z Calc'd 303, found 303.

後処理

  1. concentrationconcentrated
  2. customfurther dried under high vacuum
  3. dissolutionIt was re-dissolved in CH2Cl2 (50 mL)
  4. stirringAfter stirring at ambient temperature overnight
  5. concentrationthe mixture was concentrated in vacuo
  6. custompurified by flash column chromatography
  7. washeluting with 1:1 EtOAc and hexanes

出典と根拠

ORDレコード
ord-af352dbedee14dd0b7a2d483592d70d5
出典データセット
uspto-grants-2007_04
特許番号
US07208500B2

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