Methyl 2-((benzoylamino)methyl)-3-oxobutanoate → (2S,3R)-methyl-2-benzamidomethyl-3-hydroxybutyrate

HRID 703278

Reaktionsgleichung

Reaktionsgleichung von HRID 703278
[C:1]([NH:9][CH2:10][CH:11]([C:16](=[O:18])[CH3:17])[C:12]([O:14][CH3:15])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClC(Cl)C>[C:1]([NH:9][CH2:10][C@@H:11]([C@H:16]([OH:18])[CH3:17])[C:12]([O:14][CH3:15])=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

3

Edukt 1

HCID 11831808Methyl 2-((benzoylamino)methyl)-3-oxobutanoate

Produkt 1

HCID 10060699(2S,3R)-methyl-2-benzamidomethyl-3-hydroxybutyrateAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

In a 100 ml-volume stainless steel autoclave whose atmosphere had been displaced with nitrogen was added a solution of 2.5 g (10 mmole) of methyl 2-(N-benzoylamino)methyl-3-oxobutanoate and 184 mg (0.1 mmole) of [Ru((+)BINAP)](CLO4)2 in 18 ml of dichloroethane, and a reaction was conducted at 70° C. under a hydrogen pressure of 100 kg/cm2 for 30 hours. The reaction mixture was concentrated under reduced pressure of 20 mmHg, and the residue was purified by silica gel column chromatography using a 7/3 (by volume) mixture of hexane and isopropanol as an eluent to give 2.19 g (yield: 86.5%) of methyl (2S, 3R)-2-(N-benzoylamino)methyl-3-hydroxybutanoate having an optical purity of 90 %ee.

Aufarbeitung

  1. customwas conducted at 70° C. under a hydrogen
  2. customfor 30 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure of 20 mmHg
  4. customthe residue was purified by silica gel column chromatography
  5. additiona 7/3 (by volume) mixture of hexane and isopropanol as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-a13823069d3f4c7e8e20d15d32227bcf
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04981992

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