L-Phenylalanine → Methyl 2-[2-(3,5-dimethylphenyl)acetamido]-3-phenyl-propanoate

HRID 71018

Reaktionsgleichung

Reaktionsgleichung von HRID 71018
[CH:1]1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]1[CH:18]=[C:19]([CH2:24][C:25]([OH:27])=O)[CH:20]=[C:21]([CH3:23])[CH:22]=1.[NH2:28][C@H:29]([C:37]([OH:39])=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C)C1C=CN=CC=1.C1COCC1>[CH3:23][C:21]1[CH:20]=[C:19]([CH2:24][C:25]([NH:28][CH:29]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:37]([O:39][CH3:1])=[O:38])=[O:27])[CH:18]=[C:17]([CH3:16])[CH:22]=1

Komponenten

6

Edukt 3

HCID 6140L-PhenylalanineHCID 10868DicyclohexylcarbodiimideHCID 47494952-(3,5-Dimethylphenyl)acetic acid

Produkt 1

HCID 67042062Methyl 2-[2-(3,5-dimethylphenyl)acetamido]-3-phenyl-propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

DMAP (4-dimethylaminopyridine) (17.0 mg, 1.40 mmol) and DCC (1,3-dicyclohexylcarbodiimide)(86.2 mg, 4.19 mmol) were added to a solution of 3,5-dimethylphenylacetic acid (500 mg, 2.79 mmol) in dry THF (50 ml) were added. The mixture was stirred at rt for 30 min and then methyl ester of L-Phenylalanine (461 mg, 2.79 mmol) was added. After 48 h at rt. the crude mixture was filtered over celite and the solvent was removed under reduced pressure. The product was purified by flash chromatography (hexane/ethyl acetate 2:1) to afford (S) methyl 2-[2-(3,5-dimethylphenyl)acetamido]-3-phenyl-propanoate as white solid (70% c.y.).

Aufarbeitung

  1. additionwere added
  2. waitAfter 48 h at rt
  3. filtrationthe crude mixture was filtered over celite
  4. customthe solvent was removed under reduced pressure
  5. customThe product was purified by flash chromatography (hexane/ethyl acetate 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-42c5883df3084d1c947a4c2f72e50b0b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822698B2

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