Hydrochloric Acid → HCID 136074304, compound

HRID 1369454Notes

Reaction equation

HRID 1369454 reaction equation
C([O:3][C:4](=[O:42])[C@H:5]([CH2:35][CH2:36][C:37]([O:39]CC)=[O:38])[NH:6][C:7](=[O:34])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][S:15]([C:18]2[CH:19]=[CH:20][C:21]3[CH2:30][CH2:29][C:28]4[N:27]=[C:26]([CH3:31])[NH:25][C:24](=[O:32])[C:23]=4[C:22]=3[CH:33]=2)(=[O:17])=[O:16])=[CH:10][CH:9]=1)C.Cl>>[CH3:31][C:26]1[NH:25][C:24](=[O:32])[C:23]2[C:22]3[CH:33]=[C:18]([S:15]([NH:14][C:11]4[CH:12]=[CH:13][C:8]([C:7]([NH:6][C@H:5]([C:4]([OH:42])=[O:3])[CH2:35][CH2:36][C:37]([OH:39])=[O:38])=[O:34])=[CH:9][CH:10]=4)(=[O:16])=[O:17])[CH:19]=[CH:20][C:21]=3[CH2:30][CH2:29][C:28]=2[N:27]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 136076169HCID 136076169, compound

Product 1

HCID 136074304HCID 136074304, compoundYield 96%

Procedure

Diethyl-N-(4-((1,2,5,6-tetrahydro-3-methyl-1-oxobenzo [f]quinazolin-9-yl)sulfonamido) benzoyl)-L-glutamate (4.53 g, 7.6 mmole) was dissolved in N-NaOH (64 ml) and the solution stirred at room temperature for 4 hours. The pH of the solution was adjusted to 3.00 with 1N HCl, the solid collected by filtration, washed with water and dried under high vacuum to yield the product as an off-white solid (3.94 g 96%). 1HNMR (DMSO-d6,300 MHz) δ: 1.84-1.96 (m,1H,glu CH); 2.00-2.10 (m, 1H, glu CH); 2.32(s, 3H, CH3, superimposed over t, 2H, glu CH2); 2.71 (m, 2H, Ar CH2); 2.89 (m, 2H, Ar CH2); 4.28-4.36 (m, 1H, glu CH), 7.20 (d, J=9 Hz, 2H, Ar); 7.39 (d, J=8 Hz, 1H, Ar); 7.62 (dd, J=8.2 Hz, 1H, Ar); 7.74 (d, J=9Hz, 2H, Ar); 8.44 (d, J=8 Hz, 1H, gluNH); 9.21 (d, J=2Hz, 1H, Ar); 10.73 (s, 1H, SO2NH); 12.36 (br s, 2H, CO2H); 12.72 (br s, 1H, NH). Anal Calculated for C25H24N4O8S. 3/2H2O: C,52.91; H,4.79; N,9.87; S,5.65. Found: C,52.98; H,4.78; N,9.87; S,5.58.

Workup

  1. filtrationthe solid collected by filtration
  2. washwashed with water
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-986c82be6f5b4e4a9d404adbda015303
Source dataset
uspto-grants-2003_06
Patent number
US06579877B2

Reaction notes

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