Hydrochloric Acid → HCID 23000258, compound

HRID 398372Notes

Reaction equation

HRID 398372 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:29])[N:11]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:12]([CH3:20])=[CH:13][C:14]=1[C:15]([O:17]CC)=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.[Li+].[OH-].Cl>O>[CH2:1]([O:8][C:9]1[C:10](=[O:29])[N:11]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:12]([CH3:20])=[CH:13][C:14]=1[C:15]([OH:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 23000159HCID 23000159, compound

Product 1

HCID 23000258HCID 23000258, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-benzyloxy-4-ethoxycarbonyl-6-methyl-1-tert-butyloxycarbonylmethyl-2-pyridinone from step 2 above (1.1 g, 2.8 mmol) in 1:1 THF:H2O (20 mL) was added aqueous LiOH (3.0 mL of a 1.1 N solution, 3.3 mmol) and the resulting solution was stirred at ambient temperature for 18 h. Aqueous HCl was added (3 mL of a 1 N solution, 3 mmol) and the solvents were removed in vacuo. The residue was partitioned between water and EtOAc. The organic layer was separated and the aqueous layer was extracted four times with EtOAc. The combined organic phases were dried over Na2SO4, filtered, and the solvent was removed in vacuo to give the title compound as an amorphous solid (0.91 g; HPLC RT=15.98 min, method B).

Workup

  1. customwere removed in vacuo
  2. customThe residue was partitioned between water and EtOAc
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted four times with EtOAc
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d0ec3e84ca0a4793b3df2a253d35a562
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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