Sodium Hydroxide → ethyl (R)-2-acetylamino-3-(5,6,7,8-tetrahydro-naphthalen-2-yl)-propionate
Reaction equation
O.O.P([O-])([O-])(O)=O.[Na+].[Na+].P([O-])(O)(O)=O.[Na+].[C:16]([NH:19][CH:20]([CH2:26][C:27]1[CH:36]=[CH:35][C:34]2[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=2[CH:28]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22])(=[O:18])[CH3:17].[OH-].[Na+]>O.CC(C)=O>[C:16]([NH:19][C@H:20]([CH2:26][C:27]1[CH:36]=[CH:35][C:34]2[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=2[CH:28]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22])(=[O:18])[CH3:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
20 mL Alcalase 2.4 L FG (Novozymes A/S; DK 2880 Bagsvaerd) were added to a solution of 28.3 g (159 mmol) disodium hydrogen phosphate dihydrate in 500 mL water at a temperature of 37° C. and by the addition of sodium dihydrogen phosphate the pH was adjusted to 7.5. Then 22.0 g (76.0 mmol) ethyl 2-acetylamino-3-(5,6,7,8-tetrahydro-naphthalen-2-yl)-propionate dissolved in 130 mL acetone was added dropwise at 37° C. with stirring. The pH value of the reaction mixture was kept in the range from pH 7.4 to pH 7.6 by the addition of 1 M NaOH. After the addition had ended the mixture was stirred for 3 h at 37° C. and overnight at RT. The reaction mixture was extracted three times with tert-butylmethylether, the combined organic extracts were washed with 15% K2CO3 solution, dried and evaporated down under reduced pressure.
Workup
- additionwas added dropwise at 37° C.
- additionAfter the addition
- stirringwas stirred for 3 h at 37° C. and overnight at RT
- extractionThe reaction mixture was extracted three times with tert-butylmethylether
- washthe combined organic extracts were washed with 15% K2CO3 solution
- customdried
- customevaporated down under reduced pressure
Sources & evidence
- ORD record
- ord-d73434179e8947f2ac3b67c7b9f56736
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700589B2
Reaction notes
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