Sodium Hydroxide → [4-(1-tert-butoxycarbonylmethyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl]-acetic acid

HRID 472747Notes

Reaction equation

HRID 472747 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:13]2=[O:31])=[CH:8][CH:7]=1)C.[OH-].[Na+]>CO>[C:27]([O:26][C:24]([CH2:23][N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21](=[O:22])[N:12]([C:9]2[CH:8]=[CH:7][C:6]([CH2:5][C:4]([OH:32])=[O:3])=[CH:11][CH:10]=2)[C:13]1=[O:31])=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68589591[4-(1-tert-butoxycarbonylmethyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl]-acetic acid ethyl ester2×

Product 1

HCID 68589939[4-(1-tert-butoxycarbonylmethyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl]-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [4-(1-tert-butoxycarbonylmethyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl]-acetic acid ethyl ester (Intermediate G) (1.4 g, 3.2 mmol) in MeOH (25 ml) is treated with aqueous sodium hydroxide (0.5 M, 10 ml). After stirring at RT for 30 minutes, the MeOH is removed in vacuo and the resulting mixture is diluted with distilled water and washed with EtOAc (2×) to remove impurities. The separated aqueous phase is acidified with dilute HCl (0.1 M) to pH 3 and extracted with EtOAc (2×). The combined organic portions are dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as an off-white solid.

Workup

  1. customthe MeOH is removed in vacuo
  2. additionthe resulting mixture is diluted with distilled water
  3. washwashed with EtOAc (2×)
  4. customto remove impurities
  5. extractionextracted with EtOAc (2×)
  6. dry with materialThe combined organic portions are dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1b7fa549c05c4eb5913d4dca590dee90
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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