Sodium Hydroxide → methyl (R)-2-acetylamino-3-(3-chloro-4-hydroxy-5-methyl-phenyl)-propionate
Reaction equation
[C:1]([NH:4][CH:5]([CH2:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([OH:18])=[C:13]([Cl:19])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2].[OH-].[Na+]>O.CC(C)=O>[C:1]([NH:4][C@H:5]([CH2:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([OH:18])=[C:13]([Cl:19])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2]Participants
Conditions
- Temperature
- 37 °C
Procedure
6.0 mL Alcalase 2.4 L FG (Novozymes A/S; DK 2880 Bagsvaerd) was added to a warm solution (37° C.) of 7.2 g (40.4 mmol) Na2HPO4 dihydrate in 100 mL water and by the addition of NaH2PO4 dihydrate the pH was adjusted to 7.5. Then a solution of 5.5 g (19.2 mmol) methyl 2-acetylamino-3-(3-chloro-4-hydroxy-5-methyl-phenyl)-propionate in 50 mL acetone was added dropwise with stirring at 37° C. The pH value of the reaction mixture was kept constantly in the range from pH 7.4-7.6 by the addition of 1 M NaOH. After the addition had ended the mixture was stirred for 4 h at 37° C. After cooling to RT the reaction mixture was exhaustively extracted with MTBE, the combined organic extracts were washed with 15% K2CO3 solution and dried over Na2SO4. After the desiccant and solvent had been eliminated the crude product (1.6 g) was further reacted without purification.
Workup
- additionAfter the addition
- stirringwas stirred for 4 h at 37° C
- temperatureAfter cooling to RT the reaction mixture
- extractionwas exhaustively extracted with MTBE
- washthe combined organic extracts were washed with 15% K2CO3 solution
- dry with materialdried over Na2SO4
- customwas further reacted without purification
Sources & evidence
- ORD record
- ord-81b7ddde0b4f487aa4b0a27fae81298b
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07528129B2
Reaction notes
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