Water → HCID 59395386, compound

HRID 1097733Notes

Reaction equation

HRID 1097733 reaction equation
[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])[C:6](=[O:21])[N:5]([CH2:22][CH3:23])[C:4]=2[N:3]=1.O.[OH-].[Li+]>CO>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:6](=[O:21])[N:5]([CH2:22][CH3:23])[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 59395539HCID 59395539, compound

Product 1

HCID 59395386HCID 59395386, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of ethyl 5-(8-chloro-3-ethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoate (2.3 g, 6.7 mmol) in methanol (75 ml) was treated with water (3 ml) and lithium hydroxide (0.481 g, 20.1 mmol) and the mixture stirred at 40° C. for 17 h. The mixture was evaporated to dryness and the residue treated with 50 ml of ethyl acetate and 50 ml of water. The 2 phases were separated and the aqueous phase adjusted to pH5 using 2M aqueous hydrochloric acid. The precipitated product was filtered off and dried to yield 5-(8-chloro-3-ethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoic acid as a white solid (1.99 g, 95%).

Workup

  1. customThe mixture was evaporated to dryness
  2. additionthe residue treated with 50 ml of ethyl acetate and 50 ml of water
  3. customThe 2 phases were separated
  4. filtrationThe precipitated product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-a76f4d45b43c4ea198003b8ddc9d7cb4
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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