Sodium Hydroxide → (S)-5-methyl-3-nitromethyl-hexanoic acid ethyl ester

HRID 1034565Notes

Reaction equation

HRID 1034565 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH:6]([CH2:11][N+:12]([O-:14])=[O:13])[CH2:7][CH:8]([CH3:10])[CH3:9])[CH3:2].[OH-].[Na+]>>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C@@H:6]([CH2:11][N+:12]([O-:14])=[O:13])[CH2:7][CH:8]([CH3:10])[CH3:9])[CH3:2]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 14463328Ethyl 5-methyl-3-(nitromethyl)hexanoate

Product 1

HCID 29984078(S)-5-methyl-3-nitromethyl-hexanoic acid ethyl esterYield 43%

Procedure

100 g of 5-methyl-3-nitromethyl-hexanoic acid ethyl ester (VIII, R1=ethyl) were added to an aqueous solution of EstB (500 mL cell extract; ˜5 g total protein concentration). At a temperature of 25° C. the pH was kept at 7.0 by continuous addition of 5M aqueous NaOH. After 55% conversion (corresponds to 50.6 mL of NaOH consumption) the reaction was stopped by addition of 100 mL of ethyl acetate. 100 mL of 5M aqueous NaOH were added and the layers were separated. The aqueous layer was washed once with 100 mL of ethyl acetate. The combined organic layers were concentrated under reduced pressure to give 43 g of (S)-5-methyl-3-nitromethyl-hexanoic acid ethyl ester (VIII, R1=ethyl; ee=98%).

Workup

  1. customAfter 55% conversion (corresponds to 50.6 mL of NaOH consumption) the reaction
  2. additionwas stopped by addition of 100 mL of ethyl acetate
  3. addition100 mL of 5M aqueous NaOH were added
  4. customthe layers were separated
  5. washThe aqueous layer was washed once with 100 mL of ethyl acetate
  6. concentrationThe combined organic layers were concentrated under reduced pressure

Sources & evidence

ORD record
ord-0221fc97b51c4b36a2f8474f2ef57606
Source dataset
uspto-grants-2013_10
Patent number
US08546112B2

Reaction notes

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