Hydrochloric Acid → HCID 14326862, compound

HRID 2232885Notes

Reaction equation

HRID 2232885 reaction equation
[C:1]1([C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([CH3:11])C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)[C:19](Cl)=[O:20].[NH2:24][C@H:25]([C:33]([OH:35])=[O:34])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl>ClCCl.CN(C)C=O.C(=O)(O)[O-].[Na+].O1CCCC1>[O:20]=[C:19]([NH:24][CH:25]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:33]([OH:35])=[O:34])[CH2:11][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6140L-PhenylalanineHCID 65578Oxalyl chlorideHCID 796762,2-Diphenylpropionic acid

Product 1

HCID 14326862HCID 14326862, compoundYield 55.7%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a magnetically stirred suspension of 5.00 g (22.1 mmol) of diphenylpropionic acid in 25 ml of dry dichloromethane under nitrogen was added 2.12 ml (24.3 mmol) of oxalyl chloride followed by two drops of dimethylformamide. After stirring for one hour, the solution was rotary evaporated and the residue placed under high vacuum to further remove any remaining volatiles. The resulting yellow oil was added to a solution of 3.65 g (22.1 mmol) of racemic phenylalanine in 50 ml of saturated aqueous sodium bicarbonate and 10 ml of tetrahydrofuran. The mixture was allowed to stir for three hours while maintaining the pH at 8. The mixture was then acidified to pH 2 with concentrated hydrochloric acid and partitioned between ethyl acetate and water. The ethyl acetate layer was washed with 10% aqueous hydrochloric acid, water, brine, dried over magnesium sulfate, filtered and rotary evaporated. Recrystallization of the residue from toluene gave 4.60 g of the title compound as an off-white solid, melting point 138°-140° C.

Workup

  1. customthe solution was rotary evaporated
  2. customto further remove any remaining volatiles
  3. stirringto stir for three hours
  4. temperaturewhile maintaining the pH at 8
  5. custompartitioned between ethyl acetate and water
  6. washThe ethyl acetate layer was washed with 10% aqueous hydrochloric acid, water, brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customRecrystallization of the residue from toluene

Sources & evidence

ORD record
ord-e47235fc8c894baca49ebd2eb115a9c7
Source dataset
uspto-grants-1988_11
Patent number
US04788010

Reaction notes

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