Sodium Bicarbonate → 222834-30-2
Reaction equation
[CH2:1]([O:3][C@@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]2[C:40]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[O:34][C:33]3[C:28]2=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:20][CH:19]=1)[C:5](N[C@@H](C1C=CC=CC=1)CO)=[O:6])[CH3:2].C(=O)([O-])[OH:42].[Na+]>S(=O)(=O)(O)O.O1CCOCC1.O>[CH2:1]([O:3][C@@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]2[C:40]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[O:34][C:33]3[C:28]2=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:20][CH:19]=1)[C:5]([OH:6])=[O:42])[CH3:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
(2S)-2-Ethoxy-N-[(1S)-2-hydroxy-1-phenylethyl]-3-{4-[2-(10H-phenoxazin-10-yl)ethoxy]phenyl}propanamide (0.45 g, 0.84 mmol) was dissolved in a mixture of 1M sulphuric acid (17 ml) and dioxane/water (1:1.39 ml) and heated to 90° C. for 88 h. The pH of the mixture was adjusted to 3 by addition of an aqueous sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate (2×25 ml) and the organic phase was washed with water (50 ml), brine (25 ml), dried (Na2SO4) and evaporated. The residue was chromatographed over silica gel using a gradient of 50-75% ethyl acetate in petroleum ether to afford the title compound (0.19 g, 54%) as a white solid. mp: 89-90° C.
Workup
- extractionThe mixture was extracted with ethyl acetate (2×25 ml)
- washthe organic phase was washed with water (50 ml), brine (25 ml)
- dry with materialdried (Na2SO4)
- customevaporated
- customThe residue was chromatographed over silica gel using a gradient of 50-75% ethyl acetate in petroleum ether
Sources & evidence
- ORD record
- ord-87e2f0b8d94049e8a56a01487839d561
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07414128B2
Reaction notes
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