Aluminum isopropoxide → Methyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

HRID 1457284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1457284
[CH2:1]([C@H:8]([NH:13][C:14](=[O:17])[O:15][CH3:16])[C:9](=[O:12])[CH2:10][Cl:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-]>C(O)(C)C>[CH2:1]([C@H:8]([NH:13][C:14](=[O:17])[O:15][CH3:16])[C@H:9]([OH:12])[CH2:10][Cl:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 11143Aluminum isopropoxideHCID 9881533methyl (S)-(1-benzyl-3-chloro-2-oxo-propyl)carbamate

Produkt 1

HCID 10945089Methyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

25.57 g of methyl(S)-(1-benzyl-3-chloro-2-oxo-propyl)-carbamate were added portionwise at 22° C. to a suspension of 21.44 g of aluminum isopropoxide in 260 ml of isopropanol. The suspension was stirred at 50° C./400 mbar for 2 hours, hydrolyzed at 0° C. with 100 ml of 3N hydrochloric acid, subsequently concentrated to a volume of 125 ml, diluted with 125 ml of water, cooled to 0° C. and filtered. The residue was washed with water/isopropanol (4:1) and dried, there being obtained 13.01 g (89%) of isomerically-pure methyl(1S,2S)-(1-benzyl-3-chloro-2-hydroxy-propyl)-carbamate, m.p. 162°-163.5° C. IR (KBr): 3323 s, br. (NH, OH), 1689(C=O), 1546 s (amide II).

Aufarbeitung

  1. concentrationhydrolyzed at 0° C. with 100 ml of 3N hydrochloric acid, subsequently concentrated to a volume of 125 ml
  2. additiondiluted with 125 ml of water
  3. temperaturecooled to 0° C.
  4. filtrationfiltered
  5. washThe residue was washed with water/isopropanol (4:1)
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b7edb2ba646446b5bdfc726cb2ac11ec
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05847144

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