Sodium Hydroxide → HCID 61261489, compound

HRID 1175113Notes

Reaction equation

HRID 1175113 reaction equation
[CH3:1][C:2]([NH:8][C:9]([C:11]1[CH:16]=[N:15][CH:14]=[CH:13][N:12]=1)=[O:10])([CH3:7])[C:3]([O:5]C)=[O:4].[OH-].[Na+]>O.CO.[Cl-].[Na+].O.CCOC(C)=O>[CH3:7][C:2]([NH:8][C:9]([C:11]1[CH:16]=[N:15][CH:14]=[CH:13][N:12]=1)=[O:10])([CH3:1])[C:3]([OH:5])=[O:4]

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 68732840HCID 68732840, compound

Product 1

HCID 61261489HCID 61261489, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of methyl 2-methyl-2-[(pyrazin-2-ylcarbonyl)amino]propanoate (9.8 mmol) and 1 M NaOH in water (19.6 mL) was stirred in methanol for 6 hours. The reaction was diluted with brine and EtOAc and the layers were separated. The aqueous layer was acidified with 1 M HCl in water (28 mL) to an approximate pH˜2. The aqueous was extracted with EtOAc (3×). These three combined extracts were dried (Na2SO4), filtered and concentrated to obtain 1.96 g (96% over two steps) of the title compound. 1H NMR (300 MHz, CD3OD) δ 9.16 (d, J=1.3 Hz, 1H); 8.75 (d, J=2.4 Hz, 1H); 8.65 (dd, J=1.5, 2.4 Hz, 1H); 1.63 (s, 6H). LC/MS: Rt, =1.27 min, ES+210 (Formic Acid Method).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous was extracted with EtOAc (3×)
  3. dry with materialThese three combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-75f8a368b56f47fc8a67ad92e7787d82
Source dataset
uspto-grants-2010_11
Patent number
US07838673B2

Reaction notes

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