Hydrochloric Acid → HCID 20588791, compound

HRID 369549Notes

Reaction equation

HRID 369549 reaction equation
[OH2:1].[OH-].[Li+].[CH3:4][C@H:5]([O:12][C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][C:16](CC([O-])=O)=[C:15]([N:26]([CH3:28])[CH3:27])[CH:14]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].Cl>C1COCC1.O>[CH3:4][C@H:5]([O:12][C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][C:16]([OH:1])=[C:15]([N:26]([CH3:28])[CH3:27])[CH:14]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 70011189HCID 70011189, compound

Product 1

HCID 20588791HCID 20588791, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (226 mg, 5.38 mmol) was added to a stirred solution of compound 59 in 15 ml THF and 5 ml water. The reaction mixture was stirred for 15 minutes and was then acidified with concentrated HCl. Extracted with ether, the organic layer was washed with brine and dried over MgSO4. The crude product was purified via flash chromatography over silica gel (80/20, v/v, Hex/EtOAc). Evaporation of solvent yielded 308 mg (92%) of a viscous orange oil. This product rapidly decomposes in chloroform and should be carried on immediately to the next step.

Workup

  1. extractionExtracted with ether
  2. washthe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customThe crude product was purified via flash chromatography over silica gel (80/20, v/v, Hex/EtOAc)
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-454ea61b6bd844168f0c6394e9457b63
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Reaction notes

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