Water → N-Benzyloxycarbonyl-L-threonine phenacyl ester

HRID 1720091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1720091
[CH3:1][C@@H:2]([OH:18])[C@H:3]([NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C:4]([OH:6])=[O:5].C(N(CC)CC)C.Br[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29].O>CC(=O)OCC.C(O)(C)C>[CH2:27]([O:5][C:4](=[O:6])[C@H:3]([C@@H:2]([CH3:1])[OH:18])[NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6259Phenacyl bromideHCID 8471TriethylamineHCID 88217N-((Benzyloxy)carbonyl)-L-threonine

Produkt 1

HCID 54036068N-Benzyloxycarbonyl-L-threonine phenacyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

25.3 g (0.1 mol) of Z-L-threonine were suspended in 200 ml of EA, and 14 ml (0.1 mol) of triethylamine were added. While stirring, 19.0 g (0.1 mol) of solid ω-bromoacetophenone were added in one portion to result initially in a clear solution, which soon became cloudy. The mixture was left to stand for 2 d, diluted with 500 ml of EA and worked up as usual. The crystalline residue was dissolved in 420 ml of hot isopropanol, 300 ml of hot water were added, and the mixture was left to stand in the dark for 2 d. The long white needles which separated out were filtered off, washed and dried in air in the dark. Yield: 27.8 g (0.075 mol, 75%), melting point 129°-130° C., α!D25 =32.2° (c=2.04, EA)

Aufarbeitung

  1. customto result initially in a clear solution, which soon became cloudy
  2. waitThe mixture was left
  3. waitthe mixture was left
  4. customdark for 2 d
  5. customThe long white needles which separated out
  6. filtrationwere filtered off
  7. washwashed
  8. customdried in air in the dark
  9. customα!D25 =32.2° (c=2.04, EA)

Quellen und Nachweise

ORD-Eintrag
ord-cacd857c655b41bda55651a4371064db
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05504189

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