Benzoylecgonine → HCID 131730269, compound

HRID 1941753Notes

Reaction equation

HRID 1941753 reaction equation
[CH3:1][N:2]1[C@H:6]2[C@@H:7]([C:19]([OH:21])=[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.O[NH:23][C:24](=[O:30])[CH2:25][CH2:26][C:27]([NH2:29])=[O:28]>O1C=COC=C1.O1CCOCC1>[CH3:1][N:2]1[C@H:6]2[C@@H:7]([C:19]([OH:21])=[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.[C:24]([NH2:23])(=[O:30])[CH2:25][CH2:26][C:27]([NH2:29])=[O:28]

Participants

5

Reactant 2

HCID 448223BenzoylecgonineHCID 18381240N-hydroxysuccinamide

Product 1

HCID 131730269HCID 131730269, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 789681,4-DioxinSolvent

Procedure

Benzoylecgonine (BE) (4 mg) was dissolved in dry dioxin (500 ul) and N-hydroxysuccinamide (NHS) (4 mg) added. 1-Ethyl-3-(3-dimethylaminopropul)carbodiimide hydrochloride (8 mg) was suspended/dissolved in dioxan (1 ml) and immediately added to the mixture. The mixture was shaken at ambient temperature for 2 hours (to form BE-succinamide). To this was added diamino terminated polyethyleneglycol (mol. wt. 20,000) dissolved in 1 ml of 0.1M sodium bicarbonate solution. The solution was left overnight (about 16 hrs) and was then diluted with tris/triton buffer.

Workup

  1. additionimmediately added to the mixture

Sources & evidence

ORD record
ord-8dd9deb848e14478aac40a0c845a47ee
Source dataset
uspto-grants-2013_03
Patent number
US08389296B2

Reaction notes

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