Hydrochloric Acid → HCID 19080433, compound

HRID 865523Notes

Reaction equation

HRID 865523 reaction equation
[CH2:1]([C:5]1[CH:26]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[CH:24]=[CH:23][C:6]=1[O:7][CH:8]([C:14]1[CH:19]=[CH:18][C:17]2[O:20][CH2:21][O:22][C:16]=2[CH:15]=1)[C:9]([O:11]CC)=[O:10])[CH:2]([CH3:4])[CH3:3].[OH-].[Na+].[NH4+].[OH-].Cl>CO.C(Cl)(Cl)Cl>[CH2:1]([C:5]1[CH:26]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[CH:24]=[CH:23][C:6]=1[O:7][CH:8]([C:14]1[CH:19]=[CH:18][C:17]2[O:20][CH2:21][O:22][C:16]=2[CH:15]=1)[C:9]([OH:11])=[O:10])[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 19080364HCID 19080364, compound

Product 1

HCID 19080433HCID 19080433, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

To a solution of 1.518 g (3.66 mmol) of the product of Step A dissolved in 8.0 mL of methanol was added 1.0 mL of a 5.0 M solution of aqueous sodium hydroxide. The reaction was stirred at room temperature and monitored by TLC (80:15:1 CHCl3 --MeOH--NH4OH). After 1.5 hours the reaction was judged to be complete and the reaction mixture was adjusted to pH=5 with 1.0 N HCl. The reaction mixture was then partitioned between EtOAc and water, separated, dried (MgSO4), filtered, and evaporated. The residue was purified on a silica gel flash chromatography column eluted with CHCl3 --MeOH--NH4OH (80:15:1); evaporation of the purified fractions and drying in vacuo afforded the title compound as an amorphous foam.

Workup

  1. customThe reaction mixture was then partitioned between EtOAc and water
  2. customseparated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified on a silica gel flash chromatography column
  7. washeluted with CHCl3 --MeOH--NH4OH (80:15:1)
  8. customevaporation of the purified fractions
  9. customdrying in vacuo

Sources & evidence

ORD record
ord-ab687bc697774717995a3e2c0961c6cc
Source dataset
uspto-grants-1996_10
Patent number
US05565485

Reaction notes

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