Hydrochloric Acid → HCID 87606313, compound

HRID 1985202Notes

Reaction equation

HRID 1985202 reaction equation
C([O:3][C:4](=[O:46])[C:5]([CH3:45])([O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=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]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=3)[C:18](=[O:36])[N:17]2[CH3:37])=[CH:9][CH:8]=1)C.[OH-].[Na+].Cl>C(O)C>[F:35][C:32]([F:33])([F:34])[C:24]1[CH:23]=[C:22]([CH:27]=[C:26]([C:28]([F:29])([F:30])[F:31])[CH:25]=1)[CH2:21][N:19]1[CH2:20][CH:16]([CH2:15][CH2:14][O:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][C:5]([CH3:45])([O:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:4]([OH:46])=[O:3])=[CH:8][CH:9]=2)[N:17]([CH3:37])[C:18]1=[O:36]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 87606331HCID 87606331, compound

Product 1

HCID 87606313HCID 87606313, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the esters obtained from Step A (378 mg) in absolute ethanol (4 ml) is added 5N NaOH (1.5 ml, 7.5 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 (266 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 (266 mg.)

Sources & evidence

ORD record
ord-e1d49ba0a3e14c4c9f303344610a2398
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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