反応 #2467955

反応方程式

methyl 2-benzamidomethyl-3-ketobutyrate

isopropylalcohol

→

(2S,3R)-methyl-2-benzamidomethyl-3-hydroxybutyrate

収率 105.0%

溶媒

acetonitrile

triethanolamine

反応条件

後処理

1. 1
   その他brought up to 37° C.
2. 2
   その他over the course of the reaction that
3. 3
   ろ過filtered through a 0.25 μm syringe
4. 4
   ろ過filter
5. 5
   workup.ADDITIONwas added to the reaction mixture
6. 6
   workup.STIRRINGThe reaction mixture was stirred for another 15 minutes
7. 7
   ろ過filtered through a Celite pad (5 g in a fritted glass
8. 8
   ろ過filter) under vacuum
9. 9
   洗浄The filter cake was washed with 20 ml ethyl acetate
10. 10
    その他to separated
11. 11
    洗浄The organic layer is washed three times with 20 ml water
12. 12
    濃縮concentrated on a rotary evaporator to an oil of constant weight
13. 13
    その他After removal of ethyl acetate, toluene (10 ml)
14. 14
    workup.ADDITIONwas added
15. 15
    workup.DISTILLATIONdistilled under vacuum

実験手順

A 250 ml 3-neck flask with overhead stirrer was charged with methyl 2-benzamidomethyl-3-ketobutyrate (25 g), isopropylalcohol (37.5 ml) and 0.1 M triethanolamine(chloride)/0.04 M MgSO4 buffer pH7.2 (30 ml). The reaction mixture is stirred and temperature brought up to 37° C. using an oil bath. The reaction is started with the addition of 0.5 ml 19 g/L NADP-Na followed by 2.5 ml 30 g/L KRED of SEQ ID No. 10; both as solutions in 0.1 M triethanolamine (chloride)/0.04 M MgSO4 buffer pH7.2. The reaction progress was followed by taking 5 μl aliquots over the course of the reaction that were diluted with 1 ml acetonitrile, filtered through a 0.25 μm syringe filter and analyzed as described in Example 3. When the conversion exceeded 96% saturated aqueous sodium chloride (12.5 ml) was added to the reaction mixture, followed by 40 ml ethyl acetate. The reaction mixture was stirred for another 15 minutes, then filtered through a Celite pad (5 g in a fritted glass filter) under vacuum. The filter cake was washed with 20 ml ethyl acetate and the two phases of the filtrate allowed to separated. The organic layer is washed three times with 20 ml water and concentrated on a rotary evaporator to an oil of constant weight. After removal of ethyl acetate, toluene (10 ml) was added and distilled under vacuum. (2S,3R)-methyl-2-benzamidomethyl-3-hydroxybutyrate (26.47 g) was obtained as an oil containing ˜10% toluene as determined by 1H-NMR—CDCl3.

出典