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Acetic Acid → (S)-3-{(S)-4-Methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-pentanoylamino}-4-oxo-butyric acid

HRID 1371282
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1371282
[C:1]1([O:11][CH2:12][C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([CH:33]=[O:34])[CH2:25][C:26](=NNC(N)=O)[OH:27])=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(O)(=[O:37])C.CO>C=O.O>[C:1]1([O:11][CH2:12][C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([CH:33]=[O:34])[CH2:25][C:26]([OH:27])=[O:37])=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 887MethanolHCID 178446027(3 S)-3-[N-((1-naphthyloxy)acetyl)leucinyl]amino-4-oxobutanoic acid semicarbazone

Produkt 1

HCID 9823074(S)-3-{(S)-4-Methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-pentanoylamino}-4-oxo-butyric acidAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 712
Formaldehyde
Lösungsmittel
HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of (3S)-3-[N-((1-naphthyloxy)acetyl)leucinyl]amino-4-oxobutanoic acid semicarbazone (0.320 g, 0.68 mmol) in 37% aqueous formaldehyde(1.0 mL)-acetic acid(1.0 mL)-methanol(3.0 mL) was stirred at room temperature under nitrogen for 3.5 hrs. The resulting solution was diluted with water and extracted with EtOAc. The extract was washed with water and saturated NaCl solution, dried over anhydrous Na2SO4 and evaporated to dryness. The residue was taken up in EtOAc, filtered through Celite and evaporated to dryness. The product was taken up in a small amount of dioxane, diluted with water, frozen and lyophilized to give the title compound (0.222 g, 79%) as a fluffy white solid. TLC(EtOAc-pyridine-AcOH-H2O; 60:20:5:10) Rf=0.65.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe extract was washed with water and saturated NaCl solution
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated to dryness
  5. filtrationfiltered through Celite
  6. customevaporated to dryness
  7. additiondiluted with water
  8. temperaturefrozen

Quellen und Nachweise

ORD-Eintrag
ord-f9f3d418cfa242729fd21b2b28cc085a
Quelldatensatz
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07157430B2

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