Vinyl laurate → HCID 57065228, compound

HRID 35808Notes

Reaction equation

HRID 35808 reaction equation
[CH2:1]([CH:4]([CH:12]([OH:14])[CH3:13])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH:2]=[CH2:3].C(OC=C)(=O)CCCCCCCCCCC>>[CH2:1]([CH:4]([C@@H:12]([OH:14])[CH3:13])[C:5]([O:7][C:8]([CH3:10])([CH3:9])[CH3:11])=[O:6])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 75069Vinyl laurateHCID 14360248HCID 14360248, compound

Product 1

HCID 57065228HCID 57065228, compoundYield 45.3%

Conditions

Temperature
35 °C

Procedure

A mixture of 15.0 g of t-butyl 2-allyl-3-hydroxybutanoate as racemate, 13.7 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 9 days. After stopping the reaction, the enzyme was removed by filtration and the enzyme was washed with n-heptane on a filter paper. The filtrate was distilled away and the residue was subjected to vacuum distillation to give 6.8 g of t-butyl (3S)-2-allyl-3-hydroxybutanoate of the following formula, b.p. 79°-85° C. (5.0 mm Hg), [α]D30 =+5.0° (C=1.35, CHCl3). ##STR79## The NMR chart is shown in FIG. 9.

Workup

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

Sources & evidence

ORD record
ord-11639c4f87d5420bb254cba375d573f9
Source dataset
uspto-grants-1995_05
Patent number
US05411877

Reaction notes

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