Trifluoroacetic acid → L-Valyl-N-Methyl-L-Alanyl-L-Alanine Benzyl Ester

HRID 2254528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2254528
[CH2:1]([O:8][C:9](=[O:33])[C@H:10]([CH3:32])[NH:11][C:12](=[O:31])[C@H:13]([CH3:30])[N:14]([C:16](=[O:29])[C@H:17]([CH:26]([CH3:28])[CH3:27])[NH:18]C(OC(C)(C)C)=O)[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:8][C:9](=[O:33])[C@H:10]([CH3:32])[NH:11][C:12](=[O:31])[C@H:13]([CH3:30])[N:14]([C:16](=[O:29])[C@H:17]([CH:26]([CH3:28])[CH3:27])[NH2:18])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 14673106Boc-L-Valyl-N-Mehtyl-L-Alanyl-L-Alanine Benzyl Ester

Produkt 1

HCID 14673108L-Valyl-N-Methyl-L-Alanyl-L-Alanine Benzyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

A stirred solution of 17 g (0.0367 mole) Boc-L-valyl-N-methyl-L-alanyl-L-alanine benzyl ester in 170 ml of dry dichloromethane was cooled at -10° C. as 85 ml of trifluoroacetic acid, previously cooled at -15° C., was added. After 16 hours at -5° C., the reaction was carefully poured with good stirring into a mixture of 93 g of sodium bicarbonate, ice, and 250 ml of dichloromethane. The organic layer was separated and the aqueous layer was extracted with another 75 ml of dichloromethane. The combined organic layers were washed with 3×75 ml of saturated sodium bicarbonate solution, dried over magnesium sulfate, and evaporated to give 12.8 g (96% of theory) of crude product which was used in step 5 without further purification. FAB m.s. showed a molecular ion peak at 364.

Aufarbeitung

  1. additionwas added
  2. additionthe reaction was carefully poured
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with another 75 ml of dichloromethane
  5. washThe combined organic layers were washed with 3×75 ml of saturated sodium bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customto give 12.8 g (96% of theory) of crude product which
  9. customwas used in step 5 without further purification

Quellen und Nachweise

ORD-Eintrag
ord-b21d5bef50904eb5b4b794507c6b6a37
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05236899

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