Hydrochloric Acid → HCID 178525990, compound

HRID 2099239Notes

Reaction equation

HRID 2099239 reaction equation
[CH2:1]([N:8]1[CH:13]=[C:12]([C:14](=[O:22])[CH:15]=[C:16]([OH:21])[C:17]([O:19]C)=[O:18])[C:11](=[O:23])[N:10]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:9]1=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCOCC1>[CH2:1]([N:8]1[CH:13]=[C:12]([C:14](=[O:22])[CH:15]=[C:16]([OH:21])[C:17]([OH:19])=[O:18])[C:11](=[O:23])[N:10]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:9]1=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178501825HCID 178501825, compound

Product 1

HCID 178525990HCID 178525990, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 4-(1,3-dibenzyl-1,2,3,4-tetrahydro-2,4-dioxopyrimidin-5-yl)-2-hydroxy-4-oxobut-2-enoate (3a) (757 mg, 1.8 mmol) in dioxane (100 ml) was refluxed with 1N HCl (60 ml) for 4 h. The solution was evaporated to dryness. The resulting solid vas recrystallized from hexane and ethyl acetate (3:1) to give 617 mg a pale yellow solid. Yield as 84.2%. Mp. 186-188° C. 1HNMR (DMSO-d6): 8.89 (s, 1H), 7.57 (s, 1H), 7.24-7.36 (m, 10H), 5.16 (s, 2H), 5.02 (s, 2H). 13CNMR (DMSO-d6): 186.1, 169.0, 163.2, 159.9, 151.1, 150.2, 136.5, 135.8, 128.7, 128.4, 128.0, 127.8, 127.6, 127.3, 107.7, 100.9, 52.8, 44.2. FAB-HRMS: [M+H]+ Calcd. for C22H19N2O6 407.1243. Found 407.1248.

Workup

  1. customThe solution was evaporated to dryness
  2. customThe resulting solid vas recrystallized from hexane and ethyl acetate (3:1)

Sources & evidence

ORD record
ord-4afa3aebfaf54e5abc288f681a06f970
Source dataset
uspto-grants-2009_08
Patent number
US07569573B2

Reaction notes

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