Hydrochloric Acid → N-[[ethoxy(4-phenylbutyl)phosphinyl]acetyl]-L-tyrosine, methyl ester

HRID 434409

Reaktionsgleichung

Reaktionsgleichung von HRID 434409
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:13]([O:15][P:16]([CH2:28][C:29]([OH:31])=O)([CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:17])[CH3:14].Cl.[CH3:33][O:34][C:35](=[O:46])[C@H:36]([CH2:38][C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=1)[NH2:37]>C(#N)C.CO.C(N(CC)CC)C>[CH2:13]([O:15][P:16]([CH2:28][C:29]([NH:37][C@H:36]([C:35]([O:34][CH3:33])=[O:46])[CH2:38][C:39]1[CH:40]=[CH:41][C:42]([OH:45])=[CH:43][CH:44]=1)=[O:31])([CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:17])[CH3:14]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 70652Tyrosine Methyl EsterHCID 13136848[Ethoxy(4-phenylbutyl)phosphoryl]acetic acid

Produkt 1

HCID 131713050N-[[ethoxy(4-phenylbutyl)phosphinyl]acetyl]-L-tyrosine, methyl esterAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1,1'-Carbonyldiimidazole (0.56 g) was added portionwise to a cooled (0° C.) solution of [ethoxy(4-phenylbutyl)phosphinyl]acetic acid (0.98 g) in 70 ml of acetonitrile. This reaction mixture was stirred under argon at 0° C. for 1.5 hours. The HCl salt of L-tyrosine methyl ester (0.8 g) was dissolved in methanol and neutralized with triethylamine (0.35 g). This solution was concentrated in vacuo, dissolved in 10 ml of warm acetonitrile and added dropwise to the above solution of activated phosphinic acid ester sidechain. The reaction was stirred overnight under argon and then concentrated in vacuo. A solution of the pot residue in dichloromethane was washed (H2O, aqueous NaHCO3, brine), dried (MgSO4) and filtered to yield 1.4 g of N-[[ethoxy(4-phenylbutyl)phosphinyl]acetyl]-L-tyrosine, methyl ester.

Aufarbeitung

  1. concentrationThis solution was concentrated in vacuo
  2. dissolutiondissolved in 10 ml of warm acetonitrile
  3. additionadded dropwise to the above solution of activated phosphinic acid ester sidechain
  4. stirringThe reaction was stirred overnight under argon
  5. concentrationconcentrated in vacuo
  6. washA solution of the pot residue in dichloromethane was washed (H2O, aqueous NaHCO3, brine)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-37fd470cc21344d8ba7464aa0b158bd6
Quelldatensatz
uspto-grants-1983_08
Patentnummer
US04396772

Verknüpfte Notizen

Wird geladen…