Hydrochloric Acid → HCID 136074304, compound

HRID 23902Notes

Reaction equation

HRID 23902 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 1 N 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=9 Hz, 2H, Ar); 8.44 (d, J=8 Hz, 1H, gluNH); 9.21 (d, J=2 Hz, 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-c31206a6b6344376a798d3fdfb481a97
Source dataset
uspto-grants-2005_02
Patent number
US06855712B2

Reaction notes

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