Hydrochloric Acid → 2-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)acetic acid

HRID 535257Notes

Reaction equation

HRID 535257 reaction equation
C([O:3][C:4]([CH2:6][N:7]1[CH:22]=[CH:21][C:11]([NH:12][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:10][C:8]1=[O:9])=[O:5])C.[OH-].[Na+].Cl>O>[C:4]([CH2:6][N:7]1[CH:22]=[CH:21][C:11]([NH:12][C:13](=[O:20])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[N:10][C:8]1=[O:9])([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 120097091-Ethoxycarbonylmethyl-N4-benzoyl cytosine

Product 1

HCID 153419782-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)acetic acidYield 92.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 7 (1.38 g, 4.6 mmol) and NaOH (0.36 g, 9.2 mmol) were dissolved in water (10 mL) and the solution was stirred at room temperature for 2 h. Then the pH was adjusted to 3 using 1M HCl. The precipitate formed was separated by filtration, washed with 5 mL water and dried in vacuo to afford 3 as a white solid (1.16 g, 92%); ESI-MS m/z 274 [M+H]+; 1H NMR (400 MHz, D2O, sodium salt): δ7.78 (d, 1H, J=7.2 Hz), 7.75 (d, 2H, J=7.2H), 7.55 (t, 1H, J=7.2 Hz), 7.39 (t, 2H, J=7.2 Hz), 7.19 (d, 1H, J=7.2 Hz), 4.31 (s, 2H).

Workup

  1. customThe precipitate formed
  2. customwas separated by filtration
  3. washwashed with 5 mL water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-719e51d6cbbd45889aa3d85c17fdc9b2
Source dataset
uspto-grants-2014_10
Patent number
US08859490B2

Reaction notes

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