Hydrochloric Acid → HCID 69644808, compound

HRID 1825923Notes

Reaction equation

HRID 1825923 reaction equation
[Cl:1][C:2]1[CH:29]=[C:28]([F:30])[C:27]([F:31])=[CH:26][C:3]=1[C:4]([NH:6][C:7](=[O:25])[NH:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][C:10]=1[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[O:22])=[O:5].O.[OH-].[Li+].Cl>C1COCC1>[Cl:1][C:2]1[CH:29]=[C:28]([F:30])[C:27]([F:31])=[CH:26][C:3]=1[C:4]([NH:6][C:7](=[O:25])[NH:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[O:22])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 69644792HCID 69644792, compound

Product 1

HCID 69644808HCID 69644808, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.22 g (0.5 mmol) of methyl 4-[3-(2-chloro-4,5-difluorobenzoyl)ureido]-3-(2-methoxycarbonylvinyl)benzoate (example 11 c) were dissolved in 10 ml of THF, after which 10 ml of H2O and 0.06 g (2.4 mmol) of lithium hydroxide were added. After 2 hours, the mixture was made acid with 2 N hydrochloric acid; this was then followed by extraction with ethyl acetate and concentration. Following preparative HPLC (column: Waters Xterra ™MS C18, 5 μm, 30×100 mm, mobile phase: A: H2O+0.2% trifluoroacetic acid, B: acetonitrile, gradient: 2.5 minutes 90% A/10% B to 17.5 minutes 10% A/90% B), 0.02 g (10%) of the desired product was obtained.

Workup

  1. extractionthis was then followed by extraction with ethyl acetate and concentration

Sources & evidence

ORD record
ord-3c0835b16fe3402c95ad8366215c8365
Source dataset
uspto-grants-2006_05
Patent number
US07049341B2

Reaction notes

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