HCID 86597978, compound → HCID 86597965, compound

HRID 132673Notes

Reaction equation

HRID 132673 reaction equation
[CH2:1]([O:3][C:4](=[O:17])/[CH:5]=[C:6](\[NH:13][C:14](=[O:16])[CH3:15])/[C@H:7]([CH3:12])[C@H:8]([CH3:11])[CH2:9][CH3:10])[CH3:2]>CO>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C@@H:6]([NH:13][C:14](=[O:16])[CH3:15])[C@H:7]([CH3:12])[C@H:8]([CH3:11])[CH2:9][CH3:10])[CH3:2].[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C@H:6]([NH:13][C:14](=[O:16])[CH3:15])[C@H:7]([CH3:12])[C@H:8]([CH3:11])[CH2:9][CH3:10])[CH3:2]

Participants

4

Reactant 1

HCID 86597978HCID 86597978, compound

Product 2

HCID 86597965HCID 86597965, compoundHCID 86597977HCID 86597977, compound

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)-hept-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-heptanoic acid ethyl ester (desired diastereoisomer) to (3S,4R,5R)-3-acetylamino-4,5-dimethyl-heptanoic 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-990f6340a5954020bd9c55b0d1f56e23
Source dataset
uspto-grants-2008_06
Patent number
US07388023B2

Reaction notes

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