BOC-Ala-Gly-OBzl → (S)-2-(2-((tert-Butoxycarbonyl)amino)propanamido)acetic acid

HRID 1110693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1110693
[NH:1]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:2]([C:4]([NH:6][CH2:7][C:8]([O:10]CC1C=CC=CC=1)=[O:9])=[O:5])[CH3:3]>C(O)(=O)C.[Pd]>[NH:1]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[C@H:2]([C:4]([NH:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5])[CH3:3]

Komponenten

4

Edukt 1

HCID 10980600BOC-Ala-Gly-OBzl

Produkt 1

HCID 192414(S)-2-(2-((tert-Butoxycarbonyl)amino)propanamido)acetic acidAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

VII (16.97 g, 50 mmol) was taken in glacial acetic acid (170 ml) and hydrogenated overnight in the presence of 10% Pd/C (1.7 g) as catalyst at 40 psi. The catalyst was filtered with the aid of celite and solvent removed under reduced pressure. The residue was taken in satd. NaHCO3 solution, extracted with EtOAC (3×), cooled, acidified to pH 2.0 and re-extracted with EtOAC (3×). The combined EtOAC extracts were washed with satd. NaCl, and concentrated under reduced pressure. The residue was triturated with EtOAC: Pet. ether (1:1) and the precipitate obtained was filtered, washed with pet. ether and dried (10.9 g, yield: 87.5%), Rf4 0 52. Anal Calcd. for C10H18N2O5 .1/2H2O: C 46.50, H 7.41, N 10.84%. Found: C 46.64, H 7.41, N 10.84%.

Aufarbeitung

  1. filtrationThe catalyst was filtered with the aid of celite and solvent
  2. customremoved under reduced pressure
  3. extractionNaHCO3 solution, extracted with EtOAC (3×)
  4. temperaturecooled
  5. extractionre-extracted with EtOAC (3×)
  6. washThe combined EtOAC extracts were washed with satd
  7. concentrationNaCl, and concentrated under reduced pressure
  8. customThe residue was triturated with EtOAC
  9. customPet. ether (1:1) and the precipitate obtained
  10. filtrationwas filtered
  11. washwashed with pet. ether
  12. customdried (10.9 g, yield: 87.5%), Rf4 0 52

Quellen und Nachweise

ORD-Eintrag
ord-c65831c474ae4d56aa4733f535f28904
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04976734

Notizen zur Reaktion

Wird geladen…