Sodium Hydroxide → 4-Methyl-2-oxovaleric acid

HRID 1395560Notes

Reaction equation

HRID 1395560 reaction equation
[Na].[OH:2][CH:3]([CH2:7][CH:8]([CH3:10])[CH3:9])[C:4]([O-:6])=[O:5].[OH-].[Na+]>>[CH3:9][CH:8]([CH2:7][C@H:3]([OH:2])[C:4]([OH:6])=[O:5])[CH3:10].[CH3:9][CH:8]([CH3:10])[CH2:7][C:3](=[O:2])[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5360545SodiumHCID 219181772-Hydroxy-4-methylvalerate

Product 2

HCID 704-Methyl-2-oxovaleric acidHCID 83697Leucic acid, L-

Procedure

A 500 ml Erlenmeyer flask provided with a baffle and containing 90 ml of medium A was inoculated with Bacillus freudenreichii NRS-137KH20B (FERM-P No. 3169, ATCC 31301) from a slant culture. The incubation was carried out for 24 hours under the conditions described in Example 1. Thereafter, 3.17 g of sodium DL-2-hydroxy-4-methylvalerate were added and the fermentation was continued for 82 hours. The substrate remaining in the fermentation broth contained 15.2 mg/ml of free L-hydroxyacid (optical purity: 100%). The thus-obtained fermentation broth was then treated in an analogous manner to that described in Example 1 and there were obtained 1.18 g of crystalline L-2-hydroxy-4-methylvaleric acid of melting point 79.1° C. [[α]D25 =-26.8° (c=2 in 1-N sodium hydroxide)] and 0.7 g of 4-methyl-2-oxovaleric acid of boiling point 65°-75° C./10 mmHg.

Workup

  1. customA 500 ml Erlenmeyer flask provided with a baffle
  2. additioncontaining 90 ml of medium
  3. waitthe fermentation was continued for 82 hours
  4. additionThe thus-obtained fermentation broth was then treated in an analogous manner to that

Sources & evidence

ORD record
ord-d21ff7dfc9834b32ba09e0e32d646ac6
Source dataset
uspto-grants-1980_05
Patent number
US04204044

Reaction notes

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