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9th January 2012 @ 05:01
=== Boc-deprotection of PMY 29-1. [b]Reaction Start time: 05/01/12[/b] PMY 29-1-A (acid extraction) and -B (basic extraction) were dissolved in DCM (5 mL) in separate vials and stirred at room temperature. TFA (0.5 mL) was added and the mixture stirred for approx 2 hours. TLC showed consumption of SM (against PMY 29-1-A) for both batches. 10% NaHCO3 was added until neutral. The mixtures were extracted with EtOAc (3 × 10 mL). The extracts were washed with water (2 × 10 mL) and brine, then dried (MgSO4) and concentrated under reduced pressure. PMY 30-1-A from 29-1-A (3 mg), PMY 30-1-B from 29-1-B (8 mg) were not consistent with expected product by 1H NMR. Aqueous layers were combined and concentrated under reduced pressure. The resulting residue was triturated with EtOH (50 mL), filtered and concentrated. 1H NMR showed only traces of solvents. [i]NMR in CDCl3; could be that a more polar solvent is required. Product could be insoluble in chloroform.[/i] [b]TLC (10% MeOH/DCM) visualised with UV and vanillin:[/b] [data]1064[/data] [b]NMR:[/b] [data]1188[/data][data]1186[/data] See also: [blog]1400[/blog]
Attached Files
Scheme
Scheme
TLC
1H NMR PMY 30-1-A
1H NMR PMY 30-1-B
Comments
Re: Deprotection of Boc-Gly-4-aminoantipyrine (PMY 30-1) by OSDD Malaria
25th January 2014 @ 00:14
OSM-S-18 and OSM-S-15