Trifluoroacetic acid → (S)-2-amino-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamide

HRID 568083ノート

反応式

HRID 568083 の反応式
C(OC(=O)[NH:7][C@H:8]([C:24](=[O:30])[NH:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][C@@H:8]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:15]=1)[C:24]([NH:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:30]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 15517726(S)-[2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethyl]-carbamic acid tert-butyl ester

生成物 1

HCID 15517727(S)-2-amino-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamide収率 91.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (S)-[2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethyl]-carbamic acid tert-butyl ester (6.0 g, 14.1 mmol, Example 1, Step A) in CH2Cl2 (28 mL) was treated with trifluoroacetic acid (28 mL). The resulting solution was stirred for 20 minutes and then concentrated. The residue was diluted with EtOAc (300 mL), washed with saturated bicarbonate solution (2×300 mL) and brine (300 mL), dried over Na2SO4, and concentrated to give 4.2 g (91%) of (S)-2-Amino-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamide.

後処理

  1. concentrationconcentrated
  2. additionThe residue was diluted with EtOAc (300 mL)
  3. washwashed with saturated bicarbonate solution (2×300 mL) and brine (300 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-bdefb3e5205740d2a9e0720eaa453594
出典データセット
uspto-grants-2001_01
特許番号
US06180677B2

反応ノート

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