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

HRID 1268594ノート

反応式

HRID 1268594 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-phenylpropionylamino)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-8478c45fd80649298aa8afcd4f340fc9
出典データセット
uspto-grants-2003_04
特許番号
US06555570B2

反応ノート

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