(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 132669Notes

Reaction equation

HRID 132669 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]

Participants

3

Reactant 1

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

Product 1

HCID 25232469(3R,4R,5R)-3-Acetylamino-4,5-dimethyl-octanoic Acid Ethyl EsterYield 99.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A reactor was charged with 166 g of (4R,5R)-3-acetylamino-4,5-dimethyl-(Z)-oct-2-enoic acid ethyl ester (substrate), 2650 mL of MeOH, and 36 g of Pd/SrCO3 (lot#D25N17) catalyst. The substrate was reacted with H2 at a pressure of 50 psig to 51 psig of. During hydrogenation, additional catalyst was added at a reaction time of 67 hours (10 g). After the reaction was completed (90 hours), Pd/SrCO3 was filtered off and the filtrate was concentrated under reduced pressure to give 167 g (>99% yield) of the titled compound as an oil: 1H NMR (400 MHz, CHLOROFORM-D): 0.82 (d, J=6.8 Hz, 3H), 0.88 (t, J=7.2 Hz, 3H), 0.90 (d, J=6.6 Hz, 3H), 1.25 (t, J=7.3 Hz, 3H), 1.00-1.58 (m, 6H), 1.96 (s, 3H), 2.52 (q, J=5.2 Hz, 2H), 3.47 (s, 1H), 4.10-4.30 (m, 2H), 4.12 (t, J=7.1 Hz, 1H), 5.9 (d, 1H).

Workup

  1. customThe substrate was reacted with H2 at a pressure of 50 psig to 51 psig of
  2. additionDuring hydrogenation, additional catalyst was added at a reaction time of 67 hours (10 g)
  3. filtrationwas filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-794a683609904ad9a5eddf326cd30cc9
Source dataset
uspto-grants-2008_06
Patent number
US07388023B2

Reaction notes

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