Hydrochloric Acid → HCID 68531068, compound

HRID 1967422Notes

Reaction equation

HRID 1967422 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([S:12][CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([NH:6][NH2:7])=[O:5].[CH3:14][C@@H:15]([CH2:23][CH2:24][CH3:25])[CH:16]([CH2:19][C:20](=O)[CH3:21])[CH:17]=O.Cl.C(=O)(O)[O-].[Na+]>O.O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]([S:12][CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([NH:6][N:7]1[CH:14]=[C:15]([C@@H:16]([CH3:17])[CH2:19][CH2:20][CH3:21])[CH:23]=[C:24]1[CH3:25])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68529023HCID 68529023, compoundHCID 86642086HCID 86642086, compound

Product 1

HCID 68531068HCID 68531068, compoundYield 59.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound prepared in Example 76 (1.65 g) and (3S)-3-methyl-2-(2-oxopropyl)hexanal (1.86 g) were dissolved with tetrahydrofuran (10 mL), and 5N hydrochloric acid (0.2 mL) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 6 hours. A saturated aqueous solution of sodium bicarbonate and water were added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate. The obtained organic layer was washed by water and a saturated aqueous solution of sodium chloride. The organic layer was dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=85/15→65/35) to obtain the title compound (1.6 g) having the following physical data.

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed by water
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=85/15→65/35)

Sources & evidence

ORD record
ord-57b307ca867147efa9ded903280717e1
Source dataset
uspto-grants-2013_04
Patent number
US08420810B2

Reaction notes

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