HCID 23568779, compound → HCID 22170120, compound

HRID 1822745Notes

Reaction equation

HRID 1822745 reaction equation
[CH3:1][C:2]([CH:9]1[CH:18]2[CH2:19][CH:20]=[CH:21][CH:17]2[C:16]2[CH:15]=[C:14]([N+:22]([O-:24])=[O:23])[CH:13]=[CH:12][C:11]=2[NH:10]1)([CH3:8])[CH2:3][S:4]C(=O)C>CO.O1CCCC1.[OH-].[Na+]>[CH3:8][C:2]([CH:9]1[CH:18]2[CH2:19][CH:20]=[CH:21][CH:17]2[C:16]2[CH:15]=[C:14]([N+:22]([O-:24])=[O:23])[CH:13]=[CH:12][C:11]=2[NH:10]1)([CH3:1])[CH2:3][SH:4]

Participants

5

Reactant 1

HCID 23568779HCID 23568779, compound

Product 1

HCID 22170120HCID 22170120, compoundYield 28.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

The compound of Example 76 (134 mg) was dissolved in 15 ml of a mixed solution of methanol and tetrahydrofuran, and 15 ml of a 2 mol/l sodium hydroxide solution was added. After overnight stirring at 50° C., the reaction mixture was concentrated under reduced pressure. The resulting residue was acidified with saturated ammonium chloride solution and 2 mol/l hydrochloric acid solution, and then ethyl acetate was added. The ethyl acetate layer was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvents: hexane:ethyl acetate 4:1˜hexane:ethyl acetate=2:1˜hexane:ethyl acetate=1:1) to obtain 34 mg of the captioned compound. Its physical properties are shown below.

Workup

  1. additionwas added
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionethyl acetate was added
  4. washThe ethyl acetate layer was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (elution solvents: hexane:ethyl acetate 4:1˜hexane:ethyl acetate=2:1˜hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-66028959e267471083c0d2ebc18c0ce5
Source dataset
uspto-grants-2006_05
Patent number
US07037919B1

Reaction notes

Loading…