Sulfuric Acid → HCID 67056354, compound
Reaction equation
S(=O)(=O)(O)O.COCCOC[O:12][C:13]1[CH:33]=[CH:32][C:16]([C:17]([NH:19][CH2:20][C@H:21]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:22]([O:24][CH3:25])=[O:23])=[O:18])=[CH:15][CH:14]=1>O1CCCC1.CO>[OH:12][C:13]1[CH:33]=[CH:32][C:16]([C:17]([NH:19][CH2:20][C@H:21]([N:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)[C:22]([O:24][CH3:25])=[O:23])=[O:18])=[CH:15][CH:14]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 35 °C
Procedure
1.5 ml of 98% sulphuric acid are added to a solution of 9.6 g (24.3 mmol) of methyl (S)-3-[4-(2-methoxyethoxymethoxy)benzoylamino]-2-piperidin-1-yl-propanoate in 50 ml of tetrahydrofuran and 50 ml of methanol. The reaction medium is then stirred at 35° C. for 18 h. The solvents are concentrated under vacuum to 80% then the residue is taken up in ethyl acetate and hydrolysed. The pH is brought to 8 with a saturated aqueous solution of sodium hydrogen carbonate. The product is extracted with ethyl acetate. The organic phase is washed with water then with a saturated aqueous solution of sodium chloride, dried over magnesium sulphate, filtered and concentrated under vacuum. 6.9 g (93%) of methyl (S)-3-(4-hydroxybenzoylamino)-2-piperidin-1-ylpropanoate are obtained in the form of a white solid.
Workup
- concentrationThe solvents are concentrated under vacuum to 80%
- extractionThe product is extracted with ethyl acetate
- washThe organic phase is washed with water
- dry with materialwith a saturated aqueous solution of sodium chloride, dried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-6da8a169507c433da5d478affedc18a3
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266848B2
Reaction notes
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