Hydrochloric Acid → HCID 86590000, compound

HRID 1794938Notes

Reaction equation

HRID 1794938 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:7]1=[N:8][C:9](N)=[N:10][C:11]=2[I:15])[CH3:2].ClC(Cl)(O[C:22](=[O:28])OC(Cl)(Cl)Cl)Cl.C([N:33](CC)C(C)C)(C)C.[CH:39]([OH:52])([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.Cl.[Cl-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][N:6]1[C:14]([NH2:33])=[N:13][C:12]2[C:7]1=[N:8][C:9]([C:22]([O:52][CH:39]([C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:28])=[N:10][C:11]=2[I:15])[CH3:2]

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 7037BenzhydrolHCID 24477Sodium ThiosulfateHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 85849531(2-Amino-6-iodopurin-9-yl)-acetic acid ethyl ester

Product 1

HCID 86590000HCID 86590000, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-amino-6-iodopurine-9-yl)-acetic acid ethyl ester (13.9 g, 40 mmol) in THF (280 mL) was added triphosgene (5.34 g, 18 mmol) at 0° C. After stirring for additional 5 min, N,N-diisopropylethylamine (24.4 mL) was slowly added and the reaction mixture was stirred for 30 min at 0° C. Then benzhydrol was added and the resulting reaction mixture was allowed to warm to room temperature and stirred for additional 13 h. The reaction mixture was neutralized by addition of 1N HCl solution and saturated with sodium chloride and sodium thiosulfate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (200 mL×3). The combined organic layer was washed with brine (200 mL×2), dried over sodium sulfate, and filtered. The filtrate was evaporated in reduced pressure and the residue was purified by column chromatography to afford the titled compound (15.15g, 68%). 1H-NMR (500 MHz; DMSO-d6) δ 10.88 (bs, 1H), 8.45 (s, 1H), 7.60˜7.20 (m, 10H), 6.79 (s, 1H), 5.08 (s, 2H), 4.15 (q, 2H), 1.17 (t, 3H).

Workup

  1. stirringthe reaction mixture was stirred for 30 min at 0° C
  2. customthe resulting reaction mixture
  3. stirringstirred for additional 13 h
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (200 mL×3)
  6. washThe combined organic layer was washed with brine (200 mL×2)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customThe filtrate was evaporated in reduced pressure
  10. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-17047a4c785b44ca8b8fa67ad4f0b45c
Source dataset
uspto-grants-2006_04
Patent number
US07022851B2

Reaction notes

Loading…