Triethylamine → 2-(N-(tert.-Butoxycarbonyl)-L-phenylalanyl-aminooxy)-acetic acid

HRID 426962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 426962
Br.[NH2:2][O:3][CH2:4][C:5]([OH:7])=[O:6].[CH3:8][C:9]([O:12][C:13]([NH:15][C@H:16]([C:24](ON1C(=O)CCC1=O)=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])([CH3:11])[CH3:10].C(N(CC)CC)C>CN(C=O)C.C(O)C>[C:9]([O:12][C:13]([NH:15][C@H:16]([C:24]([NH:2][O:3][CH2:4][C:5]([OH:7])=[O:6])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])([CH3:10])([CH3:11])[CH3:8]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 107447tert-butyl (S)-(1-benzyl-2-((2,5-dioxo-1-pyrrolidinyl)oxy)-2-oxoethyl)carbamateHCID 85822048Aminooxy-acetic acid hydrobromide

Produkt 1

HCID 228088902-(N-(tert.-Butoxycarbonyl)-L-phenylalanyl-aminooxy)-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6.97 g (40.5 mmoles) of aminooxy-acetic acid hydrobromide are reacted with 14.68 g (40.5 mmoles) of BOC--Phe--OSu in 100 ml of DMF in the presence of 6.3 ml (45 mmoles) of triethylamine. Next day the reaction mixture is evaporated in vacuo, the oily residue is dissolved in 100 ml of chloroform, and the chloroform solution is washed thrice with 1 n hydrochloric acid. The organic solution is dried, evaporated in vacuo, and the oily residue is solidified with diisopropyl ether. The crude product is purified by precipitation from an ethyl acetate-diisopropyl ether solvent system. 9.70 g (74%) of BOC--Phe--OGly--OH are obtained; m.p.: 136°-137° C., Rf5 : 0.4, [α]D : -17.8° (c: 1.0, in ethanol).

Aufarbeitung

  1. customNext day the reaction mixture is evaporated in vacuo
  2. dissolutionthe oily residue is dissolved in 100 ml of chloroform
  3. washthe chloroform solution is washed thrice with 1 n hydrochloric acid
  4. customThe organic solution is dried
  5. customevaporated in vacuo
  6. customThe crude product is purified by precipitation from an ethyl acetate-diisopropyl ether solvent system
  7. custom9.70 g (74%) of BOC--Phe--OGly--OH are obtained

Quellen und Nachweise

ORD-Eintrag
ord-93db830dfaa0488fae758e9a32a52970
Quelldatensatz
uspto-grants-1979_10
Patentnummer
US04172130

Notizen zur Reaktion

Wird geladen…