Acetic Acid → HCID 135659594, compound

HRID 381579Notes

Reaction equation

HRID 381579 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[CH:14][CH:15]=[C:16]([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])[C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1.C(O)(=O)C>[OH-].[Na+]>[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[CH:14][CH:15]=[C:16]([S:17]([NH:20][C:21]4[CH:42]=[CH:41][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:23][CH:22]=4)(=[O:19])=[O:18])[C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 135659590HCID 135659590, compound

Product 1

HCID 135659594HCID 135659594, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of diethyl N-(4-((1,2-dihydro-3-methyl-1-oxobenzo[f]quinazolin-7-yl)sulfonamido)benzoyl)-L-glutamate (0.16 g, 0.3 mmoles) in 0.1 N NaOH (10 ml) was stirred at room temperature under a nitrogen atmosphere for 48 hrs, after which time the solution was acidified (pH 3.5) with acetic acid. The precipitate was collected, washed with water and dried to give N-(4-((1,2-dihydro-3-methyl-1-oxobenzo[f]-quinazolin-7-yl)sulfonamido)benzoyl)-L-glutamic acid as an off-white solid. (0.12 g, 86%) 1H NMR(DMSO-d6, 200 MHz) δ: 1.72-2.08(m, 2H, glu-CH2); 2.26(t, J=Hz, 2H, glu-CH2); 2.43(s, 3H, CH3); 4.18-4.35(m, 1H, glu-CH); 7.07(d, J=8.4 Hz, 2H, Ar); 7.63(d, J=8.3 Hz, 2H, Ar); 7.82(t, J=7.3 Hz, 1H, Ar); 7.84(d, J=8.9 Hz, 1H, Ar); 8.32(m, 2H, glu-NH+Ar); 9.07(d, J=9.3 Hz, 1H, Ar); 10.16(d, J=8.8 Hz, 1H, Ar); 12.71(br s, 1H, NH). Anal. Calculated for C25H22N4O8S.7/4H2O: C, 52.67; H, 4.51; N, 9.83. Found: C, 52.52; H, 4.36; N, 9.70.

Workup

  1. customThe precipitate was collected
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-145baf5cb2194d7a9418470f0d5a311b
Source dataset
uspto-grants-2001_10
Patent number
US06306865B1

Reaction notes

Loading…