Hydrochloric Acid → ethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionate

HRID 2230401Notes

Reaction equation

HRID 2230401 reaction equation
[OH:1][C@@H:2]([C@H:17]([OH:32])[C@H:18]([OH:31])[C@@H:19]([NH:22][C:23](=[O:30])[C@H:24]([CH2:26][CH:27]([CH3:29])[CH3:28])[NH2:25])[CH2:20][OH:21])[C:3]([NH:5][C@H:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:7][C:8]([OH:10])=[O:9])=[O:4].Cl.[CH2:34](O)[CH3:35]>>[OH:1][C@@H:2]([C@H:17]([OH:32])[C@H:18]([OH:31])[C@@H:19]([NH:22][C:23](=[O:30])[C@H:24]([CH2:26][CH:27]([CH3:28])[CH3:29])[NH2:25])[CH2:20][OH:21])[C:3]([NH:5][C@H:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:7][C:8]([O:10][CH2:34][CH3:35])=[O:9])=[O:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 10456696(S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid2×

Product 1

HCID 59902671ethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionate

Procedure

To (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid (Compound 3) (500 mg) was added a 28% solution of hydrogen chloride in ethanol (200 ml) and the mixture was stirred at room temperature for 20 hours. After concentration, the residue was subjected to silica gel column chromatography and eluted with acetonitrile-water (5:1). The effective fractions were combined and concentrated under reduced pressure. The residue was dissolved in water (10 ml) and neutralized with aqueous sodium hydrogencarbonate solution. The solution was passed through a column of DIAION HP-20SS (Mitsubishi kasei corporation), followed by elution with water-acetonitrile. The effective fractions were combined and concentrated under reduced pressure. The residue was recrystallized from chloroform-diethylether to afford the title compound (123 mg).

Workup

  1. concentrationAfter concentration
  2. washeluted with acetonitrile-water (5:1)
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in water (10 ml)
  5. washfollowed by elution with water-acetonitrile
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from chloroform-diethylether

Sources & evidence

ORD record
ord-5626da6ca69a4d3290a5bb85cf81cd60
Source dataset
uspto-grants-2002_07
Patent number
US06423869B1

Reaction notes

Loading…