Water → HCID 57565595, compound

HRID 1727030Notes

Reaction equation

HRID 1727030 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:3]=1[CH2:4][N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH2:15][CH2:16][C:17]([O:19]C)=[O:18])[C:10](=[O:21])[N:9]([CH:22]([CH3:24])[CH3:23])[C:8]=2[N:7]=[C:6]1[N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.O.[Li+].[OH-]>C(O)(=O)C>[Cl:1][C:2]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:3]=1[CH2:4][N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:10](=[O:21])[N:9]([CH:22]([CH3:24])[CH3:23])[C:8]=2[N:7]=[C:6]1[N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 57565575HCID 57565575, compound

Product 1

HCID 57565595HCID 57565595, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of methyl 3-[7-(2-chloro-6-fluorobenzyl)-3-isopropyl-2,6-dioxo-8-piperidin-1-yl-2,3,6,7-tetrahydro-1H-purin-1-yl]propanoate (9 mg, 0.018 mmol) in 150 μTHF and 50 μL H2O was treated with 18 μL 1 N LiOH. The reaction mixture was stirred at room temperature overnight and then treated with 18 μL 1 N acetic acid. The product was extracted into EtOAc and then the solvent was removed by reduced pressure. The crude product was purified by preparative thin layer chromatography (silica gel, 1 mm plate, EM Science 20×20 cm silica gel 60 F264) eluting with 100% EtOAc to give 3 mg (13% yield) of the title compound as a clear oil: 1H NMR (CDCl3, 400 MHz) 7.23-7.17 (m, 1H), 7.15-7.12 (m, 1H), 6.99-6.94 (m, 1H), 5.52 (s, 2H), 5.16-5.07 (m, 1H), 4.21 (t, 2H, J=6.9 Hz), 3.14-3.04 (m, 4H), 2.66 (t, 2H, J=6.9 Hz), 1.56-1.51 (m, 12H); MS (ESP+) m/e 492 (MH+); TLC (EtOAc:hexanes/1:1) Rf=0.61.

Workup

  1. extractionThe product was extracted into EtOAc
  2. customthe solvent was removed by reduced pressure
  3. customThe crude product was purified by preparative thin layer chromatography (silica gel, 1 mm plate, EM Science 20×20 cm silica gel 60 F264)
  4. washeluting with 100% EtOAc

Sources & evidence

ORD record
ord-4cd220b717b34587a13433fc88d88b45
Source dataset
uspto-grants-2009_02
Patent number
US07495004B2

Reaction notes

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