L-Valine → HCID 53776099, compound

HRID 1720186Notes

Reaction equation

HRID 1720186 reaction equation
C([O:3][P:4]([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])C.[NH2:11][C@H:12]([C:16]([OH:18])=[O:17])[CH:13]([CH3:15])[CH3:14].[CH:19](=O)[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)(=O)C>[CH2:9]([O:8][P:4]([O:5][CH2:6][CH3:7])([CH:19]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH:13]([CH3:15])[CH3:14])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:3])[CH3:10]

Participants

5

Reactant 3

HCID 6287L-ValineHCID 7707BenzenepropanalHCID 31215Triethyl phosphite

Product 1

HCID 53776099HCID 53776099, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Triethylphosphite (7.09 g, 42.7 mmol), L-valine (5 g, 42.7 mmol) and hydrocinnamaldehyde (5.73 g, 42.7 mmol) are heated in acetic acid (15 mL) at 80° C. for 4 h. After evaporating the solvent, the solid is dissolved in 5% sodium bicarbonate solution, washed with ether and acidified to pH =4. The aqueous mixture is extracted with ethyl acetate, dried and evaporated to afford the title compound.

Workup

  1. customAfter evaporating the solvent
  2. dissolutionthe solid is dissolved in 5% sodium bicarbonate solution
  3. washwashed with ether
  4. extractionThe aqueous mixture is extracted with ethyl acetate
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-6e078cb1e42f4d1e87c69021932430e5
Source dataset
uspto-grants-1996_04
Patent number
US05504070

Reaction notes

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