Vinyl laurate → HCID 57150665, compound

HRID 35807Notes

Reaction equation

HRID 35807 reaction equation
[CH2:1]([CH:3]([CH:11]([OH:13])[CH3:12])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH3:2].C(OC=C)(=O)CCCCCCCCCCC>>[CH2:1]([CH:3]([C@@H:11]([OH:13])[CH3:12])[C:4]([O:6][C:7]([CH3:9])([CH3:8])[CH3:10])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 75069Vinyl laurateHCID 14360132HCID 14360132, compound

Product 1

HCID 57150665HCID 57150665, compoundYield 66%

Conditions

Temperature
35 °C

Procedure

A mixture of 15.0 g of t-butyl 2-ethyl-3-hydroxybutanoate as racemate, 9.0 g of vinyl laurate and 8.0 g of Lipase P (trade name, supplied by Amano Pharmaceutical Co., Ltd.) was stirred at 35° C. for two days. After stopping the reaction, the enzyme was removed by filtration and the enzyme was washed with n-heptane on a filter paper. n-Heptane was distilled away from the filtrate and the residue was subjected to vacuum distillation to obtain 9.9 g of t-butyl (3S )-2-ethyl-3-hydroxybutanoate, b.p. 73.5°-75° C. (4.5 mm Hg), [α]D28 =+1.5° (C=1.22, CHCl3) of the following formula. ##STR73## The NMR chart is shown in FIG. 8.

Workup

  1. customthe reaction
  2. customthe enzyme was removed by filtration
  3. washthe enzyme was washed with n-heptane on a filter paper
  4. distillationn-Heptane was distilled away from the filtrate
  5. distillationthe residue was subjected to vacuum distillation

Sources & evidence

ORD record
ord-508ac3002503462dbd9a979886c71e2b
Source dataset
uspto-grants-1995_05
Patent number
US05411877

Reaction notes

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