Hydrochloric Acid → (R)-6-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([C:13]([O:15]C)=[O:14])[CH2:7][CH2:6]2.P([O-])([O-])([O-])=O.Cl.CC(=O)OCC(COC(=O)C)OC(=O)C.[OH-].[Na+].C(=O)(O)[O-].[Na+]>C(O)(C)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C@H:8]([C:13]([OH:15])=[O:14])[CH2:7][CH2:6]2Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Procedure
5 g of methyl 6-methoxy-1,2,3,4-tetrahydro-2-naphthoate are dissolved in 170 ml of tert-butanol, and 500 ml of phosphate buffer at pH 7 are added to the solution prepared in this way. The pH of the solution, which rises to 7.3-7.5, is lowered to 7.1 by the addition of 1N HCl. 2.5 g of Sigma PPL enzyme (known as porcine pancreatic lipase type II, crude, Sigma L-3126--50 U/mg using triacetin) are added to the mixture. The pH tends to drop as the reaction progresses, but is kept constant by the addition of a 0.25N solution of NaOH, the pH being controlled by an automatic titration apparatus. After 5 hours, sodium bicarbonate is added to the solution until the pH is about 8 in order to stop the reaction by inactivation of the enzyme. Extraction is carried out with ethyl ether and the two phases are separated. The organic phase contains the unreacted ester principally of (S) configuration, which can be recovered. The aqueous phase is acidified with concentrated sulfuric acid and the precipitate formed is filtered off to give 1.8 g of the title acid, which is crystallized from ethyl acetate. ee 93%.
Workup
- customprepared in this way
- customto drop as the reaction progresses
- customthe reaction by inactivation of the enzyme
- extractionExtraction
- customthe two phases are separated
- customcan be recovered
- customthe precipitate formed
- filtrationis filtered off
Sources & evidence
- ORD record
- ord-d06889c3bddb4ae48f003de3e09c1dad
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05719308
Reaction notes
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