Water → 2-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazolin-3(4H)-yl)propanoic acid

HRID 517228Notes

Reaction equation

HRID 517228 reaction equation
[OH-].[Li+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:20]3[C:19](=[O:21])[CH2:18][CH2:17][CH2:16][C:15]=3[N:14]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)[C:13](=[O:32])[N:12]2[CH:33]([CH3:38])[C:34]([O:36]C)=[O:35])=[CH:7][CH:6]=1)#[N:4].O>ClCCl>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[C:20]3[C:19](=[O:21])[CH2:18][CH2:17][CH2:16][C:15]=3[N:14]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:30])([F:31])[F:29])[CH:23]=3)[C:13](=[O:32])[N:12]2[CH:33]([CH3:38])[C:34]([OH:36])=[O:35])=[CH:9][CH:10]=1)#[N:4]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 86732348Methyl 2-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazolin-3(4H)-yl)propanoate2×

Product 1

HCID 867323492-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazolin-3(4H)-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aqueous lithium hydroxide (2 M, 1.06 mL, 2.12 mmol) is added to a solution of methyl 2-(4-(4-cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazolin-3(4H)-yl)propanoate (intermediate 58, 350 mg, 0.70 mmol), and the mixture is stirred at room temperature over night. Water and dichloromethane are added, and the phases are separated. The organic layer is discarded, and the aqueous layer is acidified with aqueous hydrogen chloride (1 M) and extracted with dichloromethane. The organic phase is dried over MgSO4 and concentrated under reduced pressure. Yield: 274 mg; ESI mass spectrum [M+H]+=484; Retention time HPLC: 0.90 min (Z018_S04).

Workup

  1. customthe phases are separated
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase is dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. custom0.90 min (Z018_S04)

Sources & evidence

ORD record
ord-87a021a7e3444fb08b80a2b847ac0240
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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