Hydrochloric Acid → HCID 66871873, compound
Reaction equation
O=C1NC2C3C1(O)C[C@@H]1C(C=3C=CC=2)=C[C@@H](C(=O)O)CN1C.[CH2:23]([N:25]([CH2:47][CH2:48][C:49]([O:51]CC)=[O:50])[C:26]([C@@H:28]1[CH:43]=[C:42]2[C@@H:32]([CH2:33][C:34]3([OH:46])[C:44]4[C:37](=[CH:38][CH:39]=[CH:40][C:41]2=4)[NH:36][C:35]3=[O:45])[N:30]([CH3:31])[CH2:29]1)=[O:27])[CH3:24].[OH-].[K+].Cl>O1CCCC1.O>[CH2:23]([N:25]([CH2:47][CH2:48][C:49]([OH:51])=[O:50])[C:26]([C@@H:28]1[CH:43]=[C:42]2[C@@H:32]([CH2:33][C:34]3([OH:46])[C:44]4[C:37](=[CH:38][CH:39]=[CH:40][C:41]2=4)[NH:36][C:35]3=[O:45])[N:30]([CH3:31])[CH2:29]1)=[O:27])[CH3:24]Participants
Procedure
To a mixture of 2-oxo-3-hydroxy lysergic acid Nethyl N-(2-carbethoxy)ethyl amide 7 (63.6 mg, 0.15 mmol) in 5 ml of tetrahydrofuran (THF) and 5 ml of water was added solid potassium hydroxide (12.5 mg, 0.22 mmol). The reaction was stirred at room temperature for 3 hours (h) until the reaction was complete by TLC analysis. The reaction solution was neutralised to pH 7 using 1N HCl and concentrated to dryness under reduced pressure. The residue was dissolved in a 10% methanol in chloroform mixture and the inorganic salts were removed by filtration. Evaporation of the solvents yielded 2-oxo-3-hydroxy lysergic acid N-ethyl N-(2-carboxy)ethyl amide (Hapten A) (45 mg, 76%) as an amorphous brown solid (Rf 0.52 on silica using 20% methanol in chloroform as eluent). υmax/cm−1 3297, 2963, 1723, 1557, 1099, 1026, 802 (FT-IR)
Workup
- concentrationconcentrated to dryness under reduced pressure
- dissolutionThe residue was dissolved in a 10% methanol in chloroform mixture
- customthe inorganic salts were removed by filtration
- customEvaporation of the solvents
Sources & evidence
- ORD record
- ord-7ab750337c684da7912f2ca767c4b27f
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115718B2
Reaction notes
Loading…