Ethanol → gamma-oxo-alpha-(phenylmethyl)-5,6-dihydro-4H-thieno[3,4-c]pyrrole-5-butanoic acid
Reaction equation
C(O)C.[O:4]=[C:5]([N:25]1[CH2:29][C:28]2=[CH:30][S:31][CH:32]=[C:27]2[CH2:26]1)[CH2:6][CH:7]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:8]([O:10]CC1C=CC=CC=1)=[O:9].[OH-].[Na+]>O1CCCC1>[O:4]=[C:5]([N:25]1[CH2:26][C:27]2=[CH:32][S:31][CH:30]=[C:28]2[CH2:29]1)[CH2:6][CH:7]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:8]([OH:10])=[O:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
15 ml of ethanol are added to a solution of 1.22 g (3 mmol) of phenylmethyl γ-oxo-α-(phenylmethyl)-5,6-dihydro-4H-thieno[3,4-c]pyrrole-5-butanoate in 15 ml of tetrahydrofuran, followed, at 0° C., by a solution of 0.36 g (9 mmol) of sodium hydroxide. After 1 h at room temperature, the medium is concentrated to about 15 ml, 15 ml of water are added and then the mixture is acidfied with 2N hydrochloric acid to pH 2 and extracted with three times 25 ml of ethyl acetate. The organic phases are pooled, washed with a saturated sodium chloride solution, dried over sodium sulphate and evaporated to dryness. The residue is triturated with diethyl ether to give 0.71 g of a white solid.
Workup
- concentrationthe medium is concentrated to about 15 ml, 15 ml of water
- additionare added
- extractionextracted with three times 25 ml of ethyl acetate
- washwashed with a saturated sodium chloride solution
- dry with materialdried over sodium sulphate
- customevaporated to dryness
- customThe residue is triturated with diethyl ether
Sources & evidence
- ORD record
- ord-53f626051fca4b698e308dea03481728
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05869518
Reaction notes
Loading…