Hydrochloric Acid → HCID 10218400, compound

HRID 1985201Notes

Reaction equation

HRID 1985201 reaction equation
C([O:3][C:4](=[O:40])[C:5]([CH3:39])([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=3)[C:18](=[O:30])[N:17]2[CH3:31])=[CH:9][CH:8]=1)C.[OH-].[Na+].Cl>C(O)C>[Cl:29][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][C:25]=1[Cl:28])[CH2:21][N:19]1[CH2:20][CH:16]([CH2:15][CH2:14][O:13][C:10]2[CH:9]=[CH:8][C:7]([CH2:6][C:5]([CH3:39])([O:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:4]([OH:40])=[O:3])=[CH:12][CH:11]=2)[N:17]([CH3:31])[C:18]1=[O:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68869791HCID 68869791, compound

Product 1

HCID 10218400HCID 10218400, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the esters obtained from Step A (320 mg) in absolute ethanol (5.5 ml) is added 5N NaOH (2.2 ml, 10.9 mmol), and the mixture stirred for 20 hours at ambient temperature. The mixture is poured into 1N HCl, then extracted with ethyl acetate (2×20 ml). The combined ethyl acetate extracts were washed with water, brine, dried (Na2SO4), and concentrated to an oil which is purified is purified by flash chromatography on a Biotage silica cartridge (gradient elution, 3:1 hexanes:ethyl acetate to 1:2 hexanes:ethyl acetate to yield a foam (180 mg.)

Workup

  1. extractionextracted with ethyl acetate (2×20 ml)
  2. washThe combined ethyl acetate extracts were washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to an oil which
  5. customis purified
  6. customis purified by flash chromatography on a Biotage silica cartridge (
  7. washgradient elution, 3:1 hexanes
  8. customethyl acetate to 1:2 hexanes:ethyl acetate to yield a foam (180 mg.)

Sources & evidence

ORD record
ord-2b51d2d4ae2240ebb00b933649171606
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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