Hydrochloric Acid → N-(4-((1,2-dihydro-3-methyl-oxobenzo[f]quinazolin-9-yl)methoxy)benzoyl)-L-glutamic acid

HRID 1884046Notes

Reaction equation

HRID 1884046 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([CH2:17][O:18][C:19]4[CH:40]=[CH:39][C:22]([C:23]([NH:25][C@H:26]([C:34]([O:36]CC)=[O:35])[CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])=[O:24])=[CH:21][CH:20]=4)[CH:15]=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1.[OH-].[Na+].Cl>C(O)C>[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([CH2:17][O:18][C:19]4[CH:40]=[CH:39][C:22]([C:23]([NH:25][C@H:26]([C:34]([OH:36])=[O:35])[CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:24])=[CH:21][CH:20]=4)[CH:15]=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 136051872diethyl N-(4-((1,2-dihydro-3-methyl-1-oxobenzo[f]quinazolin-9-yl)methoxy)benzoyl)-L-glutamate

Product 1

HCID 136024930N-(4-((1,2-dihydro-3-methyl-oxobenzo[f]quinazolin-9-yl)methoxy)benzoyl)-L-glutamic acidYield 97.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Diethyl N-(4-((1,2-dihydro-3-methyl-1-oxobenzo[f]quinazolin-9-yl)methoxy)benzoyl)-L-glutamate (0.18 g, 0.33 mmol) was suspended in ethanol (2 ml) and 0.25 N NaOH (8 ml) and stirred 1.5 hours at room temperature with intermittent periods of sonication. Additional ethanol (4 ml) and warming were required to obtain a homogeneous solution. The solution was stirred 3 hours at room temperature and then adjusted to pH 3 with 1 N HCl. The resulting suspension was filtered, and the white solid washed with water and dried under high vacuum to give N-(4-((1,2-dihydro-3-methyl-1-oxobenzo[f]quinazolin-9-yl)methoxy)benzoyl)-L-glutamic acid (0.158 g). 1H NMR (DMSO-d6, 300 MHz) δ: 1.87-2.16 (m, 2H, gluCH2), 2.35 (t, J=7 Hz, 2H, gluCH2), 2.44 (s, 3H, CH3), 4.33-4.43 (m, 1H, gluCH), 5.43 (s, 2H, CH2O), 7.16 (d, J=9 Hz, 2H, Ar), 7.64 (d, J=9 Hz, 1H, Ar), 7.74 (dd, J=8, 2 Hz, 1H, Ar), 7.88 (d, J=9 Hz, 2H, Ar), 8.08 (d, J=8 Hz, 1H, Ar), 8.26 (d, J=9 Hz, 1H, Ar), 8.47 (d, J=8 Hz, 1H, gluNH), 9.94 (s, 1H, Ar), 12.36 (br s, 2H, CO2H's), 12.59 (s, 1H, N2H). Anal. Calculated for C26H23N3O7.1/4H2O: C, 63.22; H, 4.79; N, 8.51. Found: C, 63.23; H, 4.80; N, 8.48.

Workup

  1. customto obtain a homogeneous solution
  2. filtrationThe resulting suspension was filtered
  3. washthe white solid washed with water
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-d77cde21df134c868f346a8e57f481c7
Source dataset
uspto-grants-2004_07
Patent number
US06762188B1

Reaction notes

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