Hydrochloric Acid → HCID 11374125, compound

HRID 1888309Notes

Reaction equation

HRID 1888309 reaction equation
[OH:1][C:2]([CH3:33])([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:3]/[CH:4]=[CH:5]/[C@H:6]1[C@H:10]([CH3:11])[O:9][C:8](=[O:12])[N:7]1[CH2:13][CH2:14][S:15][C:16]1[S:17][CH:18]=[C:19]([C:21]([O:23]CCCC)=[O:22])[N:20]=1.[OH-].[Na+].Cl>CO>[OH:1][C:2]([CH3:33])([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:3]/[CH:4]=[CH:5]/[C@H:6]1[C@H:10]([CH3:11])[O:9][C:8](=[O:12])[N:7]1[CH2:13][CH2:14][S:15][C:16]1[S:17][CH:18]=[C:19]([C:21]([OH:23])=[O:22])[N:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66857634HCID 66857634, compound

Product 1

HCID 11374125HCID 11374125, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the compound 44 (3.7 g) in methanol (37 mL) was added dropwise 2N aqueous sodium hydroxide solution (11 mL) at 0° C. The solution temperature was risen to room temperature and the solution was stirred for 45 minutes. After the reaction solution was cooled to 0° C., 2N hydrochloric acid was added thereto and the solution was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was purified by flush column chromatography (n-hexane:ethyl acetate=1:1) to give the title compound (2.95 g) having the following physical data.

Workup

  1. customwas risen to room temperature
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue was purified
  7. customby flush column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-eb259bfc97654f4397a5a65ad6c2d98d
Source dataset
uspto-grants-2013_08
Patent number
US08501793B2

Reaction notes

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