(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 1766845노트

반응식

HRID 1766845 반응식
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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8a5ac248821e42a887670ca5b163bcdd
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07230133B2

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