Trifluoroacetic acid → 1,1-dimethyl-2-((2R)-2-methylamino-3-phenylpropionylamino)ethyl acetate

HRID 495805ノート

反応式

HRID 495805 の反応式
[C:1]([O:4][C:5]([CH3:28])([CH3:27])[CH2:6][NH:7][C:8](=[O:26])[C@H:9]([N:17](C(OC(C)(C)C)=O)[CH3:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([O:4][C:5]([CH3:28])([CH3:27])[CH2:6][NH:7][C:8](=[O:26])[C@H:9]([NH:17][CH3:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 537951942-((2R)-2-(N-(tert-butoxycarbonyl)-N-methylamino)-3-phenylpropionylamino)-1,1-dimethylethyl acetate

生成物 1

HCID 541776851,1-dimethyl-2-((2R)-2-methylamino-3-phenylpropionylamino)ethyl acetate収率 97%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

2-((2R)-2-(N-(tert-butoxycarbonyl)-N-methylamino)-3-phenylpropionylamino)-1,1-dimethylethyl acetate (426 mg, 1.1 mmol) was dissolved in dichloromethane (2 ml) and cooled to 0° C. Trifluoroacetic acid (2 ml) was added and the reaction mixture was stirred for 15 min at 0° C. The solvent was removed in vacuo at 20° C. The residue was dissolved in dichloromethane (50 ml) and the solvent was removed in vacuo. This latter procedure was repeated two times. The crude product was purified by flash chromatography on silica (45 g), using dichloromethanelmethanol/25% aqueous ammonia (100:10:1) as eluent, to give 312 mg of 1,1-dimethyl-2((2R)-2-methylamino-3-phenylpropionylamino)ethyl acetate.

後処理

  1. customThe solvent was removed in vacuo at 20° C
  2. dissolutionThe residue was dissolved in dichloromethane (50 ml)
  3. customthe solvent was removed in vacuo
  4. customThe crude product was purified by flash chromatography on silica (45 g)

出典と根拠

ORDレコード
ord-44f41580167a430f8261f1ea0bbd8e86
出典データセット
uspto-grants-2005_09
特許番号
US06939880B2

反応ノート

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