Water → HCID 24951622, compound

HRID 1512024Notes

Reaction equation

HRID 1512024 reaction equation
[OH-].[Li+].[NH2:3][C@@H:4]([CH2:13][CH2:14][CH2:15][N:16]1[C:24]([S:25][C:26]2[C:34]([I:35])=[CH:33][C:29]3[O:30][CH2:31][O:32][C:28]=3[CH:27]=2)=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH2:36])[C:5]([O:7]C1CCCC1)=[O:6].O>O1CCCC1.O.C(O)(=O)C>[NH2:3][C@@H:4]([CH2:13][CH2:14][CH2:15][N:16]1[C:24]([S:25][C:26]2[C:34]([I:35])=[CH:33][C:29]3[O:30][CH2:31][O:32][C:28]=3[CH:27]=2)=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH2:36])[C:5]([OH:7])=[O:6]

Participants

7

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 24789153HCID 24789153, compound

Product 1

HCID 24951622HCID 24951622, compoundYield 34.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (2.88 mg, 0.12 mmol) was added to a solution of (S)-cyclopentyl 2-amino-5-(6-amino-8-(6-iodobenzo[d][1,3]dioxol-5-ylthio)-9H-purin-9-yl)pentanoate (14.0 mg, 0.02 mmol) in tetrahydrofuran (1 ml) and water (3 drops). After stirring for 12 h, 5 drops of acetic acid and water (0.1 ml) were added to the reaction mixture. The solid was collected by filtration and dried in vacuo to afford the title compound (3.6 mg) as a white solid. m/z 529 [M+H]+, 527 [M−H]−. 1H NMR (400 MHz, DMSO-d6), δ: 8.1 (1H, s), 7.4 (1H, s), 7.3 (2H, bs), 6.8 (1H, s), 6.0 (2H, s), 4.1 (2H, m), 3.1 (1H, m), 1.8-1.4 (5H, m).

Workup

  1. filtrationThe solid was collected by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-681d04f93f224288b5f9b6d9407a703f
Source dataset
uspto-grants-2012_07
Patent number
US08217050B2

Reaction notes

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