3-(Benzoyloxy)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylic acid → Cocaine

HRID 705061Notes

Reaction equation

HRID 705061 reaction equation
[CH3:1][N:2]1[CH:6]2[CH:7]([C:19]([OH:21])=[O:20])[CH:8]([O:10][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:12])[CH2:9][CH:3]1[CH2:4][CH2:5]2.ON1C(=O)CC[C:24]1=O>O1CCCC1>[CH3:1][N:2]1[C@H:6]2[C@@H:7]([C:19]([O:21][CH3:24])=[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

Participants

4

Reactant 2

HCID 23403-(Benzoyloxy)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylic acidHCID 80170N-Hydroxysuccinimide

Product 1

HCID 446220Cocaine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

For example, and not by way of limitation, 10 mg of benzoyl ecgonine in 5 ml tetrahydrofuran (“THF”) may be added to 1.1 equivalent N-hydroxysuccinimide (NHS) and 1.1 equivalent of Ethyl 3-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC). The reaction mixture may be stirred at room temperature for about 30 min. The solvent may then be removed under reduced pressure and the resultant cocaine activated ester, cocaine-NHS (a cocaine pre-hapten), may be dissolved in 0.2 ml of DMF and mixed with 5 mg of carrier Self protein in 1 ml PBS. The mixture may then be stirred for about 3 hour at about 4 C.° to provide cocaine/Self protein conjugate. The foregoing amounts may be varied depending on the desired yield of conjugate. In preferred non-limiting embodiments, the carrier Self protein may be HSA or MSA or TSA.

Workup

  1. customThe solvent may then be removed under reduced pressure
  2. dissolutionmay be dissolved in 0.2 ml of DMF
  3. additionmixed with 5 mg of carrier Self protein in 1 ml PBS
  4. stirringThe mixture may then be stirred for about 3 hour at about 4 C.°

Sources & evidence

ORD record
ord-28c8756b3b8a45b0ae1e5440c545f414
Source dataset
uspto-grants-2015_11
Patent number
US09173874B2

Reaction notes

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