Hydrochloric Acid → 5-Oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-carboxylic acid

HRID 1847008Notes

Reaction equation

HRID 1847008 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([CH:8]1[CH2:12][C:11](=[O:13])[N:10]([C:14]2[CH:15]=[CH:16][C:17]3[O:18][CH2:19][C:20](=[O:24])[NH:21][C:22]=3[N:23]=2)[CH2:9]1)=[O:7].Cl>CO>[O:13]=[C:11]1[N:10]([C:14]2[CH:15]=[CH:16][C:17]3[O:18][CH2:19][C:20](=[O:24])[NH:21][C:22]=3[N:23]=2)[CH2:9][CH:8]([C:6]([OH:7])=[O:5])[CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 867249385-Oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-carboxylic acid methyl ester

Product 1

HCID 867249395-Oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-carboxylic acidYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

An aqueous solution (0.1 ml) of lithium hydroxide monohydrate (8.62 mg, 0.206 mmol) was added to a solution of 5-oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-carboxylic acid methyl ester (40 mg, 0.137 mmol) in methanol (0.8 ml) and the mixture was stirred overnight at room temperature. The reaction solution was neutralized by adding 1N hydrochloric acid (0.206 ml), methanol was removed under reduced pressure, the obtained residue was triturated with water and the insoluble material was collected by filtration and dried to yield 32.9 mg (87%) of the title compound in the form of a colorless solid.

Workup

  1. customwas removed under reduced pressure
  2. customthe obtained residue was triturated with water
  3. filtrationthe insoluble material was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-b55dafb140f34c5badaeed57d2f21ecb
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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