Benzenepropanal → HCID 53809102, compound

HRID 1769437Notes

Reaction equation

HRID 1769437 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20](=[O:27])[C@H:21]([CH2:23][CH:24]([CH3:26])[CH3:25])[NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:28]1([CH2:34][CH2:35][CH:36]=O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C.[P:45]([O-:52])([O:49][CH2:50][CH3:51])[O:46][CH2:47][CH3:48]>C1(C)C=CC=CC=1>[CH2:12]([O:19][C:20](=[O:27])[C@H:21]([CH2:23][CH:24]([CH3:25])[CH3:26])[NH:22][CH:36]([P:45]([O:49][CH2:50][CH3:51])([O:46][CH2:47][CH3:48])=[O:52])[CH2:35][CH2:34][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 7707BenzenepropanalHCID 8471TriethylamineHCID 3780918DiethylphosphiteHCID 6451312L-Leucine, phenylmethyl ester, 4-methylbenzenesulfonate (1:1)

Product 1

HCID 53809102HCID 53809102, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5.90 g of L-leucine benzyl ester p-toluenesulfonate, 2.01 g of 3-phenylpropionaldehyde and 2.09 ml of triethylamine in 100 ml of toluene was heated to reflux in a Dean-Stark apparatus for 2 hours. The mixture was allowed to cool, and then 1.93 ml of diethyl phosphite was added to the mixture. Then the mixture was heated to reflux for 27 hours, and then allowed to cool. The mixture was successively washed with 100 ml of water, 50 ml of 1N hydrochloric acid and 50 ml of a saturated aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (chloroform: ethyl acetate=10: 1, and hexane: ethyl acetate=1: 1) to yield the title compound as a mixture of stereoisomers, a light-yellow oil (1.87 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux in a Dean-Stark apparatus for 2 hours
  3. temperatureto cool
  4. temperatureThen the mixture was heated
  5. temperatureto reflux for 27 hours
  6. temperatureto cool
  7. washThe mixture was successively washed with 100 ml of water, 50 ml of 1N hydrochloric acid and 50 ml of a saturated aqueous solution of sodium bicarbonate
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe residue was purified by silica gel chromatography (chloroform: ethyl acetate=10: 1, and hexane: ethyl acetate=1: 1)

Sources & evidence

ORD record
ord-b2e40f73791442a6ad6d1ea7933124e3
Source dataset
uspto-grants-1995_01
Patent number
US05380921

Reaction notes

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