Hydrochloric Acid → HCID 59186628, compound

HRID 731535Notes

Reaction equation

HRID 731535 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][C:5]1([O:22][CH3:23])[CH2:10][CH2:9][N:8]([C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[OH-].[Na+].Cl>O1CCOCC1>[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][C:5]1([O:22][CH3:23])[CH2:6][CH2:7][N:8]([C:11]2[CH:21]=[CH:20][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 16109134HCID 16109134, compound

Product 1

HCID 59186628HCID 59186628, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of EXAMPLE 1D (20.54 g, 55.4 mmol) in dioxane (100 mL) was treated with 1N NaOH (100 mL, 100 mmol), stirred overnight, acidified with 1N HCl, extracted with ethyl acetate (3×), dried (MgSO4), and filtered. Concentration of the filtrate gave a residue that was purified by silica gel chromatography eluting with to provide the desired product (xx g, xx %). MS (ESI) m/e 344 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customConcentration of the filtrate gave a residue that
  5. customwas purified by silica gel chromatography
  6. washeluting with

Sources & evidence

ORD record
ord-0e02d8ed382c445da803dff272348f76
Source dataset
uspto-grants-2009_09
Patent number
US07585858B2

Reaction notes

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