Vinyl laurate → HCID 57267980, compound

HRID 35801Notes

Reaction equation

HRID 35801 reaction equation
[CH3:1][CH:2]([CH:10]([OH:12])[CH3:11])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C(OC=C)(=O)CCCCCCCCCCC>>[CH3:1][CH:2]([C@@H:10]([OH:12])[CH3:11])[C:3]([O:5][C:6]([CH3:8])([CH3:7])[CH3:9])=[O:4]

Participants

3

Reactant 2

HCID 75069Vinyl laurateHCID 13724660t-Butyl 2-methyl-3hydroxybutanoate

Product 1

HCID 57267980HCID 57267980, compoundYield 43.3%

Conditions

Temperature
35 °C

Procedure

A mixture of a racemate, t-butyl 2-methyl-3hydroxybutanoate 30 g, vinyl laurate 40 g, and Lipase P (Amano Pharmaceutical Co., Ltd.) 8.0 g was stirred at 35° C. for 7 days. After stopping the reaction, the enzyme was removed by filtration and washed with n-heptane on a filter paper. n-Heptane was distilled off from the filtrate and the residue was subjected to a vacuum distillation to give 13 g of t-butyl (3S)-2-methyl-3-hydroxybutanoate of the following formula, ##STR25## and 23 g of t-butyl (3R)-2-methyl-3-dodecanoyloxy butanoate of the following formula, ##STR26##

Workup

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

Sources & evidence

ORD record
ord-c1a0e76504df473290d3e3df82f10d8a
Source dataset
uspto-grants-1995_05
Patent number
US05411877

Reaction notes

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