Hydrochloric Acid → HCID 136041243, compound

HRID 1377071Notes

Reaction equation

HRID 1377071 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([S:17]([NH:20][C:21]4[CH:42]=[CH:41][C:24]([C:25]([NH:27][C@H:28]([C:36]([O:38]CC)=[O:37])[CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])=[O:26])=[CH:23][CH:22]=4)(=[O:19])=[O:18])[CH:15]=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1.Cl>C(O)C.[OH-].[Na+]>[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([S:17]([NH:20][C:21]4[CH:22]=[CH:23][C:24]([C:25]([NH:27][C@H:28]([C:36]([OH:38])=[O:37])[CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[O:26])=[CH:41][CH:42]=4)(=[O:19])=[O:18])[CH:15]=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 135659592HCID 135659592, compound

Product 1

HCID 136041243HCID 136041243, compoundYield 0.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of diethyl N-(4-((1,2-dihydro-3-methyl-1-oxobenzo[f]quinazolin-9-yl) sulfonamido)benzoyl)-L-glutamate (0.22 g, 0.37 mol) in ethanol (3 ml) and 0.25N NaOH (12 ml) was stirred at room temperature for 3 hours. The solution was slowly acidified to pH 3 with 1N HCl and the resulting precipitate filtered, washed with water, and dried under high vacuum to give N-(4-((1,2-dihydro-3-methyl-1-oxobenzo[f]-quinazolin-9-yl) sulfonamido)benzoyl)-L-glutamic acid as a white solid (0.20 g). 1H NMR (DMSO-d6, 200 MHz) δ: 1.73-2.15 (m, 2H, glu CH2), 2.27 (t, J=7 Hz, 2H, glu CH2), 2.43 (s, 3H, CH3), 4.22-4.36 (m, 1H, glu CH), 7.20 (d, J=9 Hz, 2M, Ar), 7.69 (d, J=9 Hz, 2H, Ar), 7.76 (d, J=9 Hz, 1H, Ar), 7.90 (dd, J=9,2 Hz, 1H, Ar), 8.18 (d, J=9 Hz, 1H, Ar), 8.28 (d, J=9 Hz, 1H, Ar), 8.39 (d, J=8 Hz, 1H, glu NH), 10.44 (d, J=2 Hz, 1H, Ar), 10.86 (br s, 1H, SO2NH), 12.32 (br s, 2H, CO2H's), 12.75 (br s, 1H, N2H). Anal. Calculated for C25H22N4O8S.4/5H2O): C, 54.30; H, 4.30; N, 10.13; S, 5.80. Found: C, 54.29; H, 4.25; N, 10.13; S, 5.72.

Workup

  1. filtrationthe resulting precipitate filtered
  2. washwashed with water
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-0f1fb5347a6e4019b540dbcfbfcc68bb
Source dataset
uspto-grants-1997_09
Patent number
US05663337

Reaction notes

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