(1S,2S)-(1-([benzyloxycarbonyl-(2,4-dimethyl-benzyl)-amino]-methyl}-2-hydroxy-pentyl)-carbamic acid tert-butyl ester → (2S,3S)-2-amino-1-(2,4-dimethyl-benzylamino)-hexan-3-ol

HRID 1766845ノート

反応式

HRID 1766845 の反応式
C(OC(=O)[NH:7][C@@H:8]([CH2:14][N:15](C(OCC1C=CC=CC=1)=O)[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[CH3:24])[C@@H:9]([OH:13])[CH2:10][CH2:11][CH3:12])(C)(C)C>CO.[Pd]>[NH2:7][C@H:8]([C@@H:9]([OH:13])[CH2:10][CH2:11][CH3:12])[CH2:14][NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[CH3:24]

参加物

4

反応物 1

HCID 69287833(1S,2S)-(1-([benzyloxycarbonyl-(2,4-dimethyl-benzyl)-amino]-methyl}-2-hydroxy-pentyl)-carbamic acid tert-butyl ester

生成物 1

HCID 69287338(2S,3S)-2-amino-1-(2,4-dimethyl-benzylamino)-hexan-3-ol収率 106.8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A solution of (1S,2S)-(1-{[benzyloxycarbonyl-(2,4-dimethyl-benzyl)-amino]-methyl}-2-hydroxy-pentyl)-carbamic acid tert-butyl ester (600 mg, 1.2 mmol, see procedure 12a) in MeOH was charged with 5% Pd/C, Degussa style (120 mg), stirred under H2 (1 atm) for 12 h at RT, filtered, and concentrated in vacuo. The residue was dissolved in methylene chloride (6 mL) and the resultant solution was charged with trifluoroacetic acid (6 mL). The mixture was stirred for 3 h at RT and concentrated in vacuo. The residue was dissolved in benzene and the resultant solution was concentrated in vacuo; this procedure was repeated to provide (2S,3S)-2-amino-1-(2,4-dimethyl-benzylamino)-hexan-3-ol (321 mg). MS found: (M+H)+=251.4.

後処理

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in methylene chloride (6 mL)
  4. additionthe resultant solution was charged with trifluoroacetic acid (6 mL)
  5. stirringThe mixture was stirred for 3 h at RT
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in benzene
  8. concentrationthe resultant solution was concentrated in vacuo

出典と根拠

ORDレコード
ord-8a5ac248821e42a887670ca5b163bcdd
出典データセット
uspto-grants-2007_06
特許番号
US07230133B2

反応ノート

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