Triethylamine → (3r,4r,5r)-3-Amino-4,5-dimethyloctanoic acid

HRID 349852Notes

Reaction equation

HRID 349852 reaction equation
Cl.[NH2:2][C@@H:3]([C@H:8]([CH3:14])[C@H:9]([CH3:13])[CH2:10][CH2:11][CH3:12])[CH2:4][C:5]([OH:7])=[O:6].CCN(CC)CC>CO>[NH2:2][C@@H:3]([C@H:8]([CH3:14])[C@H:9]([CH3:13])[CH2:10][CH2:11][CH3:12])[CH2:4][C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86597975(3R,4R,5R)-3-Amino-4,5-dimethyl-octanoic Acid Hydrochloride

Product 1

HCID 11480903(3r,4r,5r)-3-Amino-4,5-dimethyloctanoic acidYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3R,4R,5R)-3-Amino-4,5-dimethyl-octanoic acid hydrochloride (92 g, 0.41 mol) was dissolved in 250 mL to 260 mL of dry MeOH in a 2 L 3-necked round bottom flask. To this solution was added Et3N (0.45 mol, 45.8 g) dropwise, which formed a white precipitate. The resulting slurry was stirred at room temperature for 15 minutes. The solvent was removed to dryness. The white solid was dispersed in 1 L of CH2Cl2 (1 L) and stirred for 1 hour. CH3CN (0.6 L) was added, and the slurry was stirred for another 0.5 hours. The slurry was filtered and the solids were washed 2× with 50 mL aliquots of CH3CN, giving 71 g of the titled compound as a white solid (92% yield; 98.8% chiral purity; 99.7% chemical purity): 1H NMR (400 MHz, CD3OD): 0.89 (t, J=7.2 Hz, 3 H), 0.91 (d, J=5.1 Hz, 3 H), 0.93 (d, J=6.6 Hz, 3 H), 1.02–1.65 (m, 4 H), 2.26 (dd, J=10.2 Hz, 1 H), 2.50 (dd, J=3.7 Hz, 1 H), 3.27 (m, J=1.6 Hz, 2 H) 3.33–3.28 (m, 1 H), 4.82 (s, 3 H).

Workup

  1. customwhich formed a white precipitate
  2. customThe solvent was removed to dryness
  3. additionThe white solid was dispersed in 1 L of CH2Cl2 (1 L)
  4. stirringstirred for 1 hour
  5. additionCH3CN (0.6 L) was added
  6. stirringthe slurry was stirred for another 0.5 hours
  7. filtrationThe slurry was filtered
  8. washthe solids were washed 2× with 50 mL aliquots of CH3CN

Sources & evidence

ORD record
ord-efde00e500e14c029f799a297baf65e9
Source dataset
uspto-grants-2007_02
Patent number
US07179934B2

Reaction notes

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