Hydrochloric Acid → (6-Benzamido-9H-purin-9-yl)acetic acid

HRID 535260Notes

Reaction equation

HRID 535260 reaction equation
[C:1]([NH:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[CH2:19][C:20]([O:22]CC)=[O:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O>[C:1]([NH:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[CH2:19][C:20]([OH:22])=[O:21])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 120097109H-Purine-9-acetic acid, 6-(benzoylamino)-, ethyl ester

Product 1

HCID 15332367(6-Benzamido-9H-purin-9-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 9 (1.63 g, 5 mmol) and NaOH (0.4 g, 10 mmol) were dissolved in water (20 mL) and the solution was stirred for 2 h at room temperature. The pH was adjusted to 3 using 1M HCl, causing precipitation of the product. The precipitate was separated by filtration, washed with water, and dried in vacuo to give 4 as a white solid: yield 1.4 g (95%); MS(+ESI): m/z 298 [M+H]+; 1H NMR (400 MHz, d-DMSO): δ11.682 (s, 1H), 9.11 (s, 1H), 8.81 (s, 1H), 8.52 (s, 1H), 8.09 (d, 2H, J=7.2 Hz), 7.67 (t, 1H, J=7.2 Hz), 7.60 (t, 2H, J=7.2 Hz), 5.16 (s, 2H); 13C NMR (400 MHz, CDCl3): δ169.43, 166.34, 152.89, 152,09, 150.29, 145.63, 133.74, 132.98, 128.45, 122.56, 44.88.

Workup

  1. customprecipitation of the product
  2. customThe precipitate was separated by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-45d9b0444415490b8bc22e3bb43e8365
Source dataset
uspto-grants-2014_10
Patent number
US08859490B2

Reaction notes

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