Hydrochloric Acid → Ammonium Hydroxide

HRID 1378856Notes

Reaction equation

HRID 1378856 reaction equation
[C:1]([C:5]1[CH:28]=[CH:27][C:8]([O:9][CH:10]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]3[O:24][CH2:25][O:26][C:18]=3[CH:17]=2)[C:11]([O:13]CC)=[O:12])=[C:7]([CH2:29][CH2:30][CH3:31])[CH:6]=1)([O:3][CH3:4])=[O:2].[OH-].[Na+].[NH4+:34].[OH-].Cl>CO.C(Cl)(Cl)Cl>[NH4+:34].[OH-:2].[C:1]([C:5]1[CH:28]=[CH:27][C:8]([O:9][CH:10]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]3[O:24][CH2:25][O:26][C:18]=3[CH:17]=2)[C:11]([OH:13])=[O:12])=[C:7]([CH2:29][CH2:30][CH3:31])[CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 19080415HCID 19080415, compound

Product 2

HCID 14923Ammonium HydroxideHCID 19080399HCID 19080399, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

To a solution of the product of Step A (4.3 g, 12 mmol) in methanol (25 mL) was added aqueous 2N NaOH (10 mL) and the reaction mixture was stirred at room temperature. The rapid progress of mono-deesterification was monitored by TLC analysis using CHCl3 --MeOH--NH4OH:(80:15:1). After 15 min, the reaction mixture was cooled to 0° C. and neutralized with aqueous 2N HCl. Methanol was removed in vacuo and the resulting mixture was acidified with aqueous 2N HCl. The oily product which precipitated was extracted into methylene chloride (3×40 mL) and the combined organic phase was washed with water, brine and then dried over MgSO4. Removal of the solvent in vacuo afforded the crude product which was then purified by flash-chromatography on silica gel using CHCl3 --MeOH--NH4OH:(80:10:1) to give desired product as the ammonium salt. The salt was treated with aqueous 1N HCl (20 mL) to provide the titled compound as a white solid (3.4 g).

Workup

  1. customMethanol was removed in vacuo
  2. customThe oily product which precipitated
  3. extractionwas extracted into methylene chloride (3×40 mL)
  4. washthe combined organic phase was washed with water, brine
  5. dry with materialdried over MgSO4
  6. customRemoval of the solvent in vacuo
  7. customafforded the crude product which
  8. customwas then purified by flash-chromatography on silica gel

Sources & evidence

ORD record
ord-bc842c79c0dd45ce9651daf62f7730e7
Source dataset
uspto-grants-1997_09
Patent number
US05668176

Reaction notes

Loading…