Hydrochloric Acid → 3-(trans-3-Cyclopropylmethoxytetrahydrofuran-4-ylamino)-6-chloro-1-carboxymethylpyrazinone

HRID 398394Notes

Reaction equation

HRID 398394 reaction equation
[CH:1]1([CH2:4][O:5][C@H:6]2[C@H:10]([NH:11][C:12]3[C:13](=[O:25])[N:14]([CH2:19][C:20]([O:22]CC)=[O:21])[C:15]([Cl:18])=[CH:16][N:17]=3)[CH2:9][O:8][CH2:7]2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>CCO>[CH:1]1([CH2:4][O:5][C@H:6]2[C@H:10]([NH:11][C:12]3[C:13](=[O:25])[N:14]([CH2:19][C:20]([OH:22])=[O:21])[C:15]([Cl:18])=[CH:16][N:17]=3)[CH2:9][O:8][CH2:7]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 700248653-(trans-3-Cyclopropylmethoxytetrahydrofuran-4-ylamino)-6-chloro-1-ethoxycarbonylmethylpyrazinone

Product 1

HCID 700236133-(trans-3-Cyclopropylmethoxytetrahydrofuran-4-ylamino)-6-chloro-1-carboxymethylpyrazinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 3-(trans-3-cyclopropylmethoxytetrahydrofuran-4-ylamino)-6-chloro-1-ethoxycarbonylmethylpyrazinone from step 6 above (0.5 g, 1.3 mmol) and aqueous NaOH (0.65 mL of a 4.0 N solution, 2.6 mmol) in EtOH (7 mL) was stirred at ambient temperature for 18 h. Aqueous HCl (0.43 mL of a 6.0 N solution, 2.6 mmol) was added and the solvents were removed in vacuo. The residue was partitioned between CH2Cl2 and water. The organic phase was separated, dried over MgSO4, filtered and the solvent was removed in vacuo to give the title compound as an amorphous solid (0.4 g; HPLC RT=5.88 min, method A).

Workup

  1. customthe solvents were removed in vacuo
  2. customThe residue was partitioned between CH2Cl2 and water
  3. customThe organic phase was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e267991e97cc48a0aa22da74c38c5c30
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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