Methyl chloroformate → (3-{2-[(Benzyl-methoxycarbonyl-amino)-methyl]-4-bromo-phenoxy}-phenyl)-acetic acid methyl ester

HRID 1969022ノート

反応式

HRID 1969022 の反応式
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH2:19][NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=1.Cl[C:30]([O:32][CH3:33])=[O:31].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH2:19][N:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:30]([O:32][CH3:33])=[O:31])[CH:6]=1

参加物

5

反応物 3

HCID 6586Methyl chloroformate2 回HCID 8471Triethylamine2 回HCID 58288498{3-[2-(Benzylamino-methyl)-4-bromo-phenoxy]-phenyl}-acetic acid methyl ester

生成物 1

HCID 58288472(3-{2-[(Benzyl-methoxycarbonyl-amino)-methyl]-4-bromo-phenoxy}-phenyl)-acetic acid methyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To {3-[2-(benzylamino-methyl)-4-bromo-phenoxy]-phenyl}-acetic acid methyl ester (0.076, 0.17 mmol) and methyl chloroformate (0.01 mL, 0.18 mmol) in CH2Cl2 (2 mL) was added triethylamine (0.02 mL, 0.18 mmol), and the reaction was stirred at room temperature for 3 hours. Some starting material was still observed by analytical LCMS, so additional methyl chloroformate (0.02 mL) and triethylamine (0.03 mL) was added, and the reaction was stirred overnight. The mixture was concentrated and purified by silica gel chromatography (10-30% EtOAc in hexanes) to give the title compound.

後処理

  1. additionwas added
  2. stirringthe reaction was stirred overnight
  3. concentrationThe mixture was concentrated
  4. custompurified by silica gel chromatography (10-30% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-537e0e6ff668484faa58e66c9bccbedc
出典データセット
uspto-grants-2013_04
特許番号
US08426449B2

反応ノート

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