Water → 2-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)propanoic acid

HRID 927211Notes

Reaction equation

HRID 927211 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([CH:15]([CH3:20])[C:16]([O:18]C)=[O:17])[C:13](=[O:21])[N:12]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)[C:11]3[CH2:32][CH2:33][C:34](=[O:35])[C:10]2=3)=[CH:5][CH:4]=1)#[N:2].[OH-].[Li+].O>O1CCOCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[N:14]([CH:15]([CH3:20])[C:16]([OH:18])=[O:17])[C:13](=[O:21])[N:12]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:29])[F:30])[CH:23]=3)[C:11]3[CH2:32][CH2:33][C:34](=[O:35])[C:10]2=3)=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 90311249Methyl 2-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)propanoate2×

Product 1

HCID 903110912-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 2-(4-(4-cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-3(2H,4H,5H)-yl)propanoate (intermediate 27, 125 mg, 0.26 mmol) in 1,4-dioxane (3 mL) is treated with aqueous lithium hydroxide (2.0 M, 390 μL, 0.78 mmol), and the mixture is stirred at room temperature over night. Water is added, and the mixture is extracted with dichloromethane. The aqueous phase is acidified with 1M aqueous hydrogen chloride and extracted with dichloromethane. The combined organic layers are dried over Na2SO4 and concentrated under reduced pressure. Yield: 91 mg; ESI mass spectrum: [M+H]+=470; Retention time HPLC: 0.85 min (Z018_S04).

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layers are dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. custom0.85 min (Z018_S04)

Sources & evidence

ORD record
ord-c18a98429dc54da3abe9e153c81b75a3
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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