Hydrochloric Acid → HCID 20640389, compound

HRID 1531796Notes

Reaction equation

HRID 1531796 reaction equation
[OH-].[Na+].[CH2:3]([N:6]1[C@H:11]([CH3:12])[CH2:10][N:9]([C@H:13]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[S:28][CH:29]=[C:30]([C:32]([O:34]CC)=[O:33])[N:31]=3)=[CH:23][CH:22]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)[C@@H:8]([CH3:37])[CH2:7]1)[CH:4]=[CH2:5].CO.Cl>O1CCOCC1>[CH2:3]([N:6]1[C@H:11]([CH3:12])[CH2:10][N:9]([C@H:13]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[S:28][CH:29]=[C:30]([C:32]([OH:34])=[O:33])[N:31]=3)=[CH:23][CH:22]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)[C@@H:8]([CH3:37])[CH2:7]1)[CH:4]=[CH2:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 9913535HCID 9913535, compound

Product 1

HCID 20640389HCID 20640389, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Aqueous sodium hydroxide solution (3 ml, 2N) was added to a solution of the compound from Example 37 (580 mg), in dioxan (6 ml) and methanol (3 ml) and the reaction stirred at room temperature for 3 hours. The reaction mixture was acidified to pH 5 using 2N hydrochloric acid then evaporated to dryness in vacuo. The residue was purified by column chromatography over silica gel using gradient elution (85/15/2.5-80/20/3 dichloromethane/methanol/ammonium hydroxide). This material was further purified on a polystyrene reverse phase resin using gradient elution (100/0-50/50 water/acetonitrile). The acetonitrile was evaporated in vacuo and the remaining aqueous solution was frozen and lyophilised to afford the title compound, 410 mg.

Workup

  1. customthen evaporated to dryness in vacuo
  2. customThe residue was purified by column chromatography over silica gel using gradient elution (85/15/2.5-80/20/3 dichloromethane/methanol/ammonium hydroxide)
  3. customThis material was further purified on a polystyrene reverse phase resin
  4. washelution (100/0-50/50 water/acetonitrile)
  5. customThe acetonitrile was evaporated in vacuo
  6. temperaturethe remaining aqueous solution was frozen

Sources & evidence

ORD record
ord-7581b78030fd4083bf625bf07853ea5e
Source dataset
uspto-grants-2001_03
Patent number
US06200978B1

Reaction notes

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