(+-)-Penicillamine → 2-Amino-3-methyl-3-((2,4,6-trimethoxyphenyl)methylthio)butanoic acid

HRID 480078

反応式

HRID 480078 の反応式
[NH2:1][CH:2]([C:6]([CH3:9])([SH:8])[CH3:7])[C:3]([OH:5])=[O:4].FC(F)(F)C(O)=O.[CH3:17][O:18][C:19]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[C:20]=1[CH2:21]O>C(Cl)Cl>[NH2:1][CH:2]([C:6]([CH3:9])([S:8][CH2:21][C:20]1[C:23]([O:29][CH3:30])=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:19]=1[O:18][CH3:17])[CH3:7])[C:3]([OH:5])=[O:4]

参加物

5

反応物 3

HCID 4727(+-)-PenicillamineHCID 6422Trifluoroacetic acidHCID 6025152,4,6-Trimethoxybenzyl alcohol

生成物 1

HCID 235083652-Amino-3-methyl-3-((2,4,6-trimethoxyphenyl)methylthio)butanoic acid収率 95%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A suspension of 2-amino-3-methyl-3-sulfanylbutanoic acid (D-penicillamine) (5.0 g, 34 mmol) in CH2Cl2 (150 mL) was cooled to 0° C. Trifluoroacetic acid (54 mL, 703 mmol) was added dropwise over a period of 5 min. Then 2,4,6-trimethoxy-benzyl alcohol (6.64 g, 34 mmol) in CH2Cl2 (137 mL) was added dropwise at 0° C. with stirring. Stirring was continued for 1 hour at 0° C. and then for 2 hours at room temperature. The solvent was removed in vacuo and the residue was dried under high vacuum for 3 hours. The crude red solid was recrystallized from 1:1:1 CH2Cl2/MeOH/EtOAc to give the title compound (10.5 g, 95%) as a white solid. 1H-NMR (300 MHz, CDCl3) δ 6.10 (s, 2H), 3.84 (s, 6H), 3.76 (s, 3H), 3.40-4.10 (m, 3H), 1.69 (s, 3H), 1.23 (s, 3H); mass spectrum (API-TIS) m/z 330 (MH+).

後処理

  1. stirringStirring
  2. waitfor 2 hours at room temperature
  3. customThe solvent was removed in vacuo
  4. customthe residue was dried under high vacuum for 3 hours
  5. customThe crude red solid was recrystallized from 1:1:1 CH2Cl2/MeOH/EtOAc

出典と根拠

ORDレコード
ord-5f9081e52a454fd78bd251a34444683b
出典データセット
uspto-grants-2003_11
特許番号
US06649629B2

関連ノート

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