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

HRID 1034565노트

반응식

HRID 1034565 반응식
[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]

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-0221fc97b51c4b36a2f8474f2ef57606
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546112B2

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