Water → HCID 69827838, compound
Reaction equation
CO[C@H]1[C@@H]2[O:8][C:9](C)([CH3:11])[O:10][C@@H:6]2[C@@H:5]([C:13]2[O:14][C:15]([CH2:18][CH3:19])=[CH:16][N:17]=2)O1.F[C:21](F)(F)[C:22]([OH:24])=[O:23].O.[C:28]([O:31][C:32](=[O:34])[CH3:33])(=[O:30])[CH3:29]>N1C=CC=CC=1>[C:22]([O:24][C@@H:29]1[C@H:6]([O:10][C:9](=[O:8])[CH3:11])[C@@H:5]([C:13]2[O:14][C:15]([CH2:18][CH3:19])=[CH:16][N:17]=2)[O:30][C@H:28]1[O:31][C:32](=[O:34])[CH3:33])(=[O:23])[CH3:21]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22 °C
Procedure
To 2-[(3aR,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-ethyl-1,3-oxazole (0.83 g) was added 9:1 trifluoroacetic acid:water (3.56 ml), and the mixture was stirred at 20° C. for 3.5 hours. The solvents were removed in vacuo to give an orange/brown oil. This material was dissolved in pyridine (7 ml), under nitrogen, acetic anhydride (2.76 ml) was added and the mixture was stirred at 22° C. for 18 h. The mixture was concentrated in vacuo, diluted with ethyl acetate (50 ml) and washed with 1 M HCl (50 ml), saturated aqueous sodium bicarbonate (3×50 ml) and brine (50 ml); the organic layer was dried (MgSO4) and the solvent evaporated to dryness to furnish the title compound as a brown/orange oil (0.854 g)
Workup
- customThe solvents were removed in vacuo
- customto give an orange/brown oil
- concentrationThe mixture was concentrated in vacuo
- additiondiluted with ethyl acetate (50 ml)
- washwashed with 1 M HCl (50 ml), saturated aqueous sodium bicarbonate (3×50 ml) and brine (50 ml)
- dry with materialthe organic layer was dried (MgSO4)
- customthe solvent evaporated to dryness
Sources & evidence
- ORD record
- ord-c6885529450d498ea2f7755fc354a3d3
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06677316B2
Reaction notes
Loading…