Methanol → (s)-5-Methyl-3-nitromethyl-hexanoic acid sodium salt

HRID 1034567Notes

Reaction equation

HRID 1034567 reaction equation
[OH-].[Na+:2].CO.C([O:7][C:8](=[O:19])[CH2:9][C@@H:10]([CH2:15][N+:16]([O-:18])=[O:17])[CH2:11][CH:12]([CH3:14])[CH3:13])C>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Na+:2].[CH3:13][CH:12]([CH3:14])[CH2:11][C@H:10]([CH2:15][N+:16]([O-:18])=[O:17])[CH2:9][C:8]([O-:19])=[O:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 29984078(S)-5-methyl-3-nitromethyl-hexanoic acid ethyl ester

Product 1

HCID 87239756(s)-5-Methyl-3-nitromethyl-hexanoic acid sodium salt

Reagents, catalysts & solvents 1

HCID 62657Potassium Phosphate, TribasicSolvent

Procedure

In a beaker 100 mg of EstC (lyophilized) were dissolved/suspended in 10 mL of potassium phosphate buffer (1 mM, pH 7.2). The pH drops to pH ˜6.8 and was adjusted to pH=7.4 with aqueous NaOH (0.1 M). Then 250 μL of methanol and 200 mg of 5-methyl-3-nitromethyl-hexanoic acid ethyl ester (VIII, R1=ethyl) were added and the pH was kept at 7.4 by continuous addition of aqueous NaOH (0.1M). After 45% conversion (corresponding to 4.0 mL of 0.1M NaOH consumption) the reaction was stopped by addition of 10 mL of ethyl acetate. The layers were separated and the aqueous layer was extracted once more with 10 mL of ethyl acetate. Then the aqueous layer was concentrated to give the title compound with an ee of 98%.

Workup

  1. customAfter 45% conversion (corresponding to 4.0 mL of 0.1M NaOH consumption) the reaction
  2. additionwas stopped by addition of 10 mL of ethyl acetate
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted once more with 10 mL of ethyl acetate
  5. concentrationThen the aqueous layer was concentrated

Sources & evidence

ORD record
ord-cdc73814ccc542d68db084df397b1100
Source dataset
uspto-grants-2013_10
Patent number
US08546112B2

Reaction notes

Loading…