Hydrochloric Acid → N2-isoButyryl-9-carboxymethylguanine

HRID 535263Notes

Reaction equation

HRID 535263 reaction equation
[C:1]([NH:6][C:7]1[NH:8][C:9](=[O:22])[C:10]2[N:11]=[CH:12][N:13]([CH2:16][C:17]([O:19]CC)=[O:18])[C:14]=2[N:15]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].[OH-].[Na+].Cl>O>[C:1]([NH:6][C:7]1[NH:8][C:9](=[O:22])[C:10]2[N:11]=[CH:12][N:13]([CH2:16][C:17]([OH:19])=[O:18])[C:14]=2[N:15]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 136386266HCID 136386266, compound

Product 1

HCID 135432204N2-isoButyryl-9-carboxymethylguanine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 11 (3.07 g, 10 mmol) and NaOH (0.8 g, 20 mmol) were dissolved in water (20 mL). The mixture was stirred at room temperature for 2 h. The pH was adjusted to 3 using 1M HCl, to obtain a white precipitate. The solution was filtered off, and the precipitate was washed with a small amount of cold water and dried in vacuo to give 5 as a white solid: yield 2.65 g (95%); MS(+ESI): m/z 280 [M+H]+; 1H NMR (400 MHz, d-DMSO): δ13.32 (s, 1H), 12.06 (s, 1H), 11.64 (s, 1H), 7.93 (s, 1H), 4.88 (s, 2H), 2.74 (septet, 1H, J=6.8 Hz), 1.10 (d, 6H, J=6.8 Hz); 13C NMR (400 MHz, CDCl3): δ180.63, 169.52, 155.29, 149.47, 148.52, 140.78, 120.17, 44.88, 39.38, 19.33.

Workup

  1. customto obtain a white precipitate
  2. filtrationThe solution was filtered off
  3. washthe precipitate was washed with a small amount of cold water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-47ea879c32d04f809cdd4315fed80385
Source dataset
uspto-grants-2014_10
Patent number
US08859490B2

Reaction notes

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