Ammonia → Benzoic Acid

HRID 962884Notes

Reaction equation

HRID 962884 reaction equation
[CH3:1][N:2]1[C@H:6]2[C@@H:7]([C:19]([O:21][CH3:22])=[O:20])[C@@H:8]([O:10][C:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[O:12])[CH2:9][C@@H:3]1[CH2:4][CH2:5]2.[CH3:23][N:24]1[CH:28]2[CH:29]([C:41]([OH:43])=[O:42])[CH:30]([O:32][C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:34])[CH2:31][CH:25]1[CH2:26][CH2:27]2.[CH3:44][O:45][C:46]([C@H:48]1[C@@H:55]([O:56][C:57]([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)=[O:58])[CH2:54][C@H:52]2[NH:53][C@@H:49]1[CH2:50][CH2:51]2)=[O:47].N>O.CO.C(OCC)(=O)C.C(N(CC)CC)C.C(Cl)(Cl)Cl>[CH3:1][N:2]1[C@H:6]2[C@@H:7]([C:19]([O:21][CH3:22])=[O:20])[C@@H:8]([O:10][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:12])[CH2:9][C@@H:3]1[CH2:4][CH2:5]2.[CH3:23][N:24]1[CH:28]2[CH:29]([C:41]([OH:43])=[O:42])[CH:30]([O:32][C:33]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[O:34])[CH2:31][CH:25]1[CH2:26][CH2:27]2.[C:57]([OH:58])(=[O:56])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1.[CH3:44][O:45][C:46]([C@H:48]1[C@@H:55]([O:56][C:57]([C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=2)=[O:58])[CH2:54][C@H:52]2[NH:53][C@@H:49]1[CH2:50][CH2:51]2)=[O:47]

Participants

13

Reactant 4

HCID 222AmmoniaHCID 23403-(Benzoyloxy)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylic acidHCID 446220CocaineHCID 644007(-)-Norcocaine

Product 4

HCID 243Benzoic AcidHCID 23403-(Benzoyloxy)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylic acidHCID 446220CocaineHCID 644007(-)-Norcocaine

Reagents, catalysts & solvents 5

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Plasma samples were aliquoted and non-radioactive cocaine, benzoyl ecgonine, and norcocaine were added in order to assist in the UV visualization of the compounds. Samples were then applied to silica TLC plates which were developed in two solvent systems: methanol, chloroform, and triethylamine (3:1:0.1); and ethyl acetate, methanol, water, and concentrated ammonia (85:10:3:1). Metabolites were identified by reference to control compounds run on the same plates. The bands were scraped off the plates and 3H-containing compounds were detected through scintillation counting. From the counts obtained the amount of cocaine, benzoyl ecgonine, benzoic acid, and norcocaine as percent of total counts was determined. The total radioactivity in the plasma was determined by scintillation counting of whole plasma. Benzoic acid is detected as a metabolite when cocaine degrades into ecgonine methyl ester and benzoic acid, and so is equimolar to the ecgonine methyl ester metabolite.

Sources & evidence

ORD record
ord-323f7d63c08046be9da1dbb38e3b6db3
Source dataset
uspto-grants-1998_06
Patent number
US05760184

Reaction notes

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