Vinyl laurate → methyl (3S)-2-methyl-3-hydroxypentanoate
Reaction equation
[CH3:1][CH:2]([CH:7]([OH:10])[CH2:8][CH3:9])[C:3]([O:5][CH3:6])=[O:4].C(OC=C)(=O)CCCCCCCCCCC>>[CH3:1][CH:2]([C@@H:7]([OH:10])[CH2:8][CH3:9])[C:3]([O:5][CH3:6])=[O:4]Participants
3
Conditions
- Temperature
- 35 °C
Procedure
A mixture of 7.2 g of methyl 2-methyl-3-hydroxypentanoate, 11.1 g of vinyl laurate, and 4.0 g of Lipase P (trade name, Amano Pharmaceutical Co., Ltd.) was stirred at 35° C. for 5 days. After stopping the reaction, the enzyme was removed by filtration and washed with n-heptane on a filter paper. n-Heptane was distilled away from the filtrate and the residue was subject to vacuum distillation to give 5.6 g of methyl (3S)-2-methyl-3-hydroxypentanoate of the following formula, [α]D20 =+3.8°(C=1.26, CHCl3). ##STR81## In addition, 3.6 g of methyl (3R)-2-methyl-3-dodecanoyloxypentanoate was obtained. αhd D=0.
Workup
- customthe reaction
- customthe enzyme was removed by filtration
- washwashed with n-heptane on a filter paper
- distillationn-Heptane was distilled away from the filtrate
- distillationthe residue was subject to vacuum distillation
Sources & evidence
- ORD record
- ord-ad0c75d40178466f9708bac22a830a60
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05411877
Reaction notes
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