Trifluoroacetic acid → 3-((2R)-2-(methylamino)-3-phenylpropionylamino)propyl acetate

HRID 366226ノート

反応式

HRID 366226 の反応式
[C:1]([O:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:27])[C@H:10]([N:18](C(OC(C)(C)C)=O)[CH3:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([O:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:27])[C@H:10]([NH:18][CH3:19])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 539060843-((2R)-2-(N-tert-butoxycarbonyl-N-methylamino)-3-phenylpropionylamino)propyl acetate

生成物 1

HCID 540549383-((2R)-2-(methylamino)-3-phenylpropionylamino)propyl acetate収率 94.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 3-((2R)-2-(N-tert-butoxycarbonyl-N-methylamino)-3-phenyl-propionylamino)propyl acetate (862 mg, 2.28 mmol) in dichloromethane (3 mL) was cooled to 0° C. Trifluoroacetic acid (3 mL) was added. The solution was stirred for 10 min. The solvents were removed in vacuo without warming. The residue was dissolved in dichloromethane (50 mL) and the solvent was removed in vacuo. The procedure was repeated twice. The crude product was purified by flash chromatography on silica (70 g) with dichloromethane/methanol/25% ammonia in water (100:10:1) to give 602 mg of 3-((2R)-2-(methylamino)-3-phenylpropionylamino)propyl acetate.

後処理

  1. customThe solvents were removed in vacuo
  2. temperaturewithout warming
  3. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  4. customthe solvent was removed in vacuo
  5. customThe crude product was purified by flash chromatography on silica (70 g) with dichloromethane/methanol/25% ammonia in water (100:10:1)

出典と根拠

ORDレコード
ord-d1801ff2bcd144d191adb8b22f8980d2
出典データセット
uspto-grants-2000_10
特許番号
US06127391

反応ノート

読み込み中…