Hydrochloric Acid → HCID 22222406, compound

HRID 1794939Notes

Reaction equation

HRID 1794939 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][N:6]1[C:14]([NH2:15])=[N:13][C:12]2[C:7]1=[N:8][C:9]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=[N:10][C:11]=2[I:16])C.O.[OH-].[Li+].Cl>O1CCCC1.O>[CH2:20]([O:19][C:17]([C:9]1[N:8]=[C:7]2[C:12]([N:13]=[C:14]([NH2:15])[N:6]2[CH2:5][C:4]([OH:27])=[O:3])=[C:11]([I:16])[N:10]=1)=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86590001HCID 86590001, compound

Product 1

HCID 22222406HCID 22222406, compoundYield 104.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of [2-(benzyloxycarbonyl)-amino-6-iodo-purine-9-yl]-acetic acid ethyl ester (10.02 g, 20.8 mmol) in tetrahydrofuran (50 mL) and water (50 mL) was added lithium hydroxide hydrate (2.83 g, 20.8 mmol) at 10° C. The resulting reaction mixture was stirred for 30 min. Then the mixture was acidified to pH=3 by adding 1N HCl. The precipitated solid was filtered off, washed with water and ethyl ether, and dried in vacuo to give the title compound (9.81 g). 1H-NMR (500 MHz; DMSO-d6) δ 10.75 (s, 1H), 8.44 (s, 1H), 7.50˜7.30 (m, 5H), 5.17 (s, 2H), 4.97 (s, 2H).

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe precipitated solid was filtered off
  3. washwashed with water and ethyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-14eb6744ad0740efbb03c41676b7491e
Source dataset
uspto-grants-2006_04
Patent number
US07022851B2

Reaction notes

Loading…