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

HRID 2083809

Reaktionsgleichung

Reaktionsgleichung von HRID 2083809
[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]>C1COCC1.[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 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

BOC-Ala-Gly-OBzl (101 g.) was dissolved in THF (500 ml.) and hydrogenized with 5% palladium/carbon (7 g.). After 6 hours, the catalyst was removed, concentrated, dissolved in THF (800 ml.), then again hydrogenized with 5% palladium/carbon. After 4 hours, the catalyst was removed and concentrated in vacuo, and the residue was solidified by treating with n-hexane. The solid residue was recrystallized by ethyl acetate - THF - n-hexane to obtain BOC-Ala-Gly-OH (72 g., Yield: 97.4%, m.p.: 129° - 132° C.). TLC: one spot (solvent system 3). [α]D28 = -8.87° (c=1, DMF).

Aufarbeitung

  1. customthe catalyst was removed
  2. concentrationconcentrated
  3. dissolutiondissolved in THF (800 ml.)
  4. waitAfter 4 hours
  5. customthe catalyst was removed
  6. concentrationconcentrated in vacuo
  7. additionby treating with n-hexane
  8. customThe solid residue was recrystallized by ethyl acetate - THF - n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-9cb84593f6cd438798a593b001ad76ed
Quelldatensatz
uspto-grants-1978_04
Patentnummer
US04086221

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