Hydrochloric Acid → 3-(1-Methylsulfonyl-trans-4-(2-pyridyl)-pyrrolidin-3-ylamino)-6-chloro-1-carboxymethylpyrazinone

HRID 398404Notes

Reaction equation

HRID 398404 reaction equation
[CH3:1][S:2]([N:5]1[CH2:9][C@@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[C@H:7]([NH:16][C:17]2[C:18](=[O:30])[N:19]([CH2:24][C:25]([O:27]CC)=[O:26])[C:20]([Cl:23])=[CH:21][N:22]=2)[CH2:6]1)(=[O:4])=[O:3].[OH-].[Na+].Cl>CCO>[CH3:1][S:2]([N:5]1[CH2:9][C@@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[C@H:7]([NH:16][C:17]2[C:18](=[O:30])[N:19]([CH2:24][C:25]([OH:27])=[O:26])[C:20]([Cl:23])=[CH:21][N:22]=2)[CH2:6]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 120962303-(1-Methylsulfonyl-trans-4-(2-pyridyl)-pyrrolidin-3-ylamino)-6-chloro-1-ethoxycarbonylmethylpyrazinone

Product 1

HCID 120962343-(1-Methylsulfonyl-trans-4-(2-pyridyl)-pyrrolidin-3-ylamino)-6-chloro-1-carboxymethylpyrazinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(1-methylsulfonyl-trans-4-(2-pyridyl)-pyrrolidin-3-ylamino)-6-chloro-1-ethoxycarbonylmethylpyrazinone from step 11 above (0.20 g, 0.47 mmol) and aqueous NaOH (0.18 mL of a 4.0 N solution, 0.71 mmol) in EtOH (7 mL) was stirred at ambient temperature for 2 h. Aqueous HCl (0.12 mL of a 6.0 N solution, 0.72 mmol) was added, and the solvents were removed in vacuo to give the title compound as an amorphous solid containing NaCl (0.2 g, HPLC RT=3.99 min, method A).

Workup

  1. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-4313e0adceb74583a5f876acb9fde661
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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