(4R,5R)-3-Acetylamino-4,5-dimethyl-(Z)-oct-2-enoic Acid Ethyl Ester → (3R,4R,5R)-3-Acetylamino-4,5-dimethyl-octanoic Acid Ethyl Ester

HRID 132672Notes

Reaction equation

HRID 132672 reaction equation
[CH2:1]([O:3][C:4](=[O:18])/[CH:5]=[C:6](\[NH:14][C:15](=[O:17])[CH3:16])/[C@H:7]([CH3:13])[C@H:8]([CH3:12])[CH2:9][CH2:10][CH3:11])[CH3:2]>CO>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C@@H:6]([NH:14][C:15](=[O:17])[CH3:16])[C@H:7]([CH3:13])[C@H:8]([CH3:12])[CH2:9][CH2:10][CH3:11])[CH3:2].[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C@H:6]([NH:14][C:15](=[O:17])[CH3:16])[C@H:7]([CH3:13])[C@H:8]([CH3:12])[CH2:9][CH2:10][CH3:11])[CH3:2]

Participants

4

Reactant 1

HCID 25232468(4R,5R)-3-Acetylamino-4,5-dimethyl-(Z)-oct-2-enoic Acid Ethyl Ester

Product 2

HCID 25232469(3R,4R,5R)-3-Acetylamino-4,5-dimethyl-octanoic Acid Ethyl EsterHCID 86597976(3S,4R,5R)-3-acetylamino-4,5-dimethyl-octanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ten mL ampoules were each charged with 20 mg of (4R,5R)-3-acetylamino-4,5-dimethyl-(Z)-oct-2-enoic acid ethyl ester (substrate), 2 mL of MeOH, and approximately 10 mg of catalyst. The ampoules were placed in a multi-reactor, purged with hydrogen, then pressurized to 20 psig with hydrogen and shaken at room temperature for 18 hours. For each ampoule following reaction, the solids were removed by filtration and the filtrate was analyzed by chiral GC (CHIRASIL-DEX CB, 140° C. isothermal). The table below provides conversion and ratio of (3R,4R,5R)-3-acetylamino-4,5-dimethyl-octanoic acid ethyl ester (desired diastereoisomer) to (3S,4R,5R)-3-acetylamino-4,5-dimethyl-octanoic acid ethyl ester (undesired diastereoisomer) for various hydrogenation catalysts.

Workup

  1. customThe ampoules were placed in a multi-reactor
  2. custompurged with hydrogen
  3. customreaction
  4. customthe solids were removed by filtration
  5. customwas analyzed by chiral GC (CHIRASIL-DEX CB, 140° C. isothermal)

Sources & evidence

ORD record
ord-bbd26abc469141e9bb885f90719730e5
Source dataset
uspto-grants-2008_06
Patent number
US07388023B2

Reaction notes

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