Isopropylamine → HCID 86754029, compound
Reaction equation
C(N([CH2:6][CH3:7])CC)C.[O:8]=[CH:9][C@H:10]([C@@H:12]([C@@H:14]([C@H:16]([CH3:18])[OH:17])[OH:15])[OH:13])[OH:11].[CH:19](N)([CH3:21])[CH3:20].[NH4+:23].[OH-:24]>CN(C)C=O>[O:8]=[CH:9][C@H:10]([C@@H:12]([C@@H:14]([C@H:16]([CH3:18])[OH:17])[OH:15])[OH:13])[OH:11].[CH:19]([C:6](=[CH2:7])[C:9]([NH2:23])=[O:24])([CH3:21])[CH3:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of pNAS (1.0 g, 5.91 mmol) in dimethylformamide (DMF, 50 mL) was added triethylamine (1.0 mL), followed by the dropwise addition of the L-fucose derivative 22 (356 mg, 1.18 mmol, 20 mol % with respect to pNAS). The solution was stirred at room temperature for 16 h, and subsequently heated to 40° C. for 18 h. The solution was cooled and isopropylamine (233 mg, 25 mol % with respect to pNAS) was added as a solution in DMF (1 mL). The solution was stirred at 40° C. for a further 24 h, cooled and added to a solution of conc. NH4OH (20 mL). The clear solution was stirred at room temperature for 12 h, followed by dialysis against water using dialysis tubing with a cut-off of 12,000-14,000 kD. The product was recovered by lyophilization. Yield 82%.
Workup
- temperaturesubsequently heated to 40° C. for 18 h
- temperatureThe solution was cooled
- stirringThe solution was stirred at 40° C. for a further 24 h
- temperaturecooled
- stirringThe clear solution was stirred at room temperature for 12 h
- customfollowed by dialysis against water using dialysis tubing with a cut-off of 12,000-14,000 kD
- customThe product was recovered by lyophilization
Sources & evidence
- ORD record
- ord-0f738fcf5fe242ff88d931960828d7bf
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06187762B1
Reaction notes
Loading…