3(S)-Isopropyl-5(S)-{1 (S)-azido-3(S)-isopropyl-4(R,S)-acetoxy-4-[4-(3-benzyloxypropyloxy)-3-(3-methoxypropyloxy)-phenyl]-butyl}-tetrahydrofuran-2-one → 3(S)-isopropyl-5(S)-{1(S)-amino-3(S)-isopropyl-4-[4-(3-hydroxy-propyloxy)-3-(3-methoxypropyloxy)-phenyl]-butyl)-tetrahydrofuran-2-one

HRID 1779814Notes

Reaction equation

HRID 1779814 reaction equation
[CH:1]([C@@H:4]1[CH2:8][C@@H:7]([C@@H:9]([N:44]=[N+]=[N-])[CH2:10][C@@H:11]([CH:41]([CH3:43])[CH3:42])[CH:12](OC(=O)C)[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][O:23]CC3C=CC=CC=3)=[C:15]([O:31][CH2:32][CH2:33][CH2:34][O:35][CH3:36])[CH:14]=2)[O:6][C:5]1=[O:47])([CH3:3])[CH3:2]>C(O)C>[CH:1]([C@@H:4]1[CH2:8][C@@H:7]([C@@H:9]([NH2:44])[CH2:10][C@@H:11]([CH:41]([CH3:43])[CH3:42])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][OH:23])=[C:15]([O:31][CH2:32][CH2:33][CH2:34][O:35][CH3:36])[CH:14]=2)[O:6][C:5]1=[O:47])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 1317195753(S)-Isopropyl-5(S)-{1 (S)-azido-3(S)-isopropyl-4(R,S)-acetoxy-4-[4-(3-benzyloxypropyloxy)-3-(3-methoxypropyloxy)-phenyl]-butyl}-tetrahydrofuran-2-one

Product 1

HCID 540120703(S)-isopropyl-5(S)-{1(S)-amino-3(S)-isopropyl-4-[4-(3-hydroxy-propyloxy)-3-(3-methoxypropyloxy)-phenyl]-butyl)-tetrahydrofuran-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 151 mg of 3(S)-isopropyl-5(S)-{1(S)-azido-3(S)-isopropyl-4(R,S)-acetoxy-4-[4-(3-benzyloxypropyloxy)-3-(3-methoxypropyloxy)-phenyl]-butyl}-tetrahydrofuran-2-one in 10 ml of ethanol is hydrogenated under normal pressure and at room temperature in the presence of 70 mg of PdO for 170 hours. The reaction mixture is filtered and concentrated by evaporation, and the residue is dissolved in 10 ml of ethanol and is again hydrogenated for 24 hours in the presence of 140 mg of PdO under normal pressure and at room temperature. Filtration and concentration by evaporation yield the title compound in the form of a crude product: Rf (dichloromethane/methanol)=0.32; HPLC Rt =11.72 minutes; FAB-MS (M+H)+ =480. The compound is used in the next step without being purified.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated by evaporation
  3. dissolutionthe residue is dissolved in 10 ml of ethanol
  4. filtrationFiltration and concentration
  5. customby evaporation

Sources & evidence

ORD record
ord-72ba63095159477f88c16bc47d479aca
Source dataset
uspto-grants-1997_05
Patent number
US05627182

Reaction notes

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