(S)-methyl 3-((S)-1-phenylethylamino)butanoate → HCID 11830202, Verbindung

HRID 1637046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637046
C[O:2][C:3](=O)[CH2:4][C@@H:5]([NH:7][C@@H:8]([CH3:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:6].C[Mg]Br>C(OCC)C>[CH3:15][C@H:8]([N:7]1[C@@H:5]([CH3:6])[CH2:4][C:3]1=[O:2])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

4

Edukt 2

HCID 11096167(S)-methyl 3-((S)-1-phenylethylamino)butanoateHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 11830202HCID 11830202, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution compound (35) from Example 21 (1.00 mmol) in anhydrous diethyl ether (5 ml) at 0° C. was added slowly, dropwise, 3.0 M methylmagnesium bromide (1.10 mmol). The resulting solution was stirred for 10 minutes and the reaction was then quenched by addition of pH7 buffer. Diethyl ether (20 ml) was added, whereafter the solution was washed with water (20 ml) and brine (20 ml), dried (magnesium sulphate) and filtered. The solvent was removed under reduced pressure to afford the title compound (41) as a clear oil which was subjected to flash chromatography on silica gel. [α]D21 -68.9 (c 1.61, CHCl3); νmax (CHCl3)/cm-1 1742 s (C=O), δH (300 MHz; CDCl3) 7.34-7.23(5H, m, Ph), 4.92 (1H, q, J=7.2, PhCHCH3), 3.51 (1H, m, CH3CHCH2); 2.97, 2.46 (2H, ABX system, JAB =14.4, JAX =5.1, JBX =2.4, CH2CO), 1.63 (3H, d, J=7.2, PhCHCH3), 1.25 (3H, d, J=6.1, CH3CHCH2); δC (50 MHz; CDCl3) 166.90 (C=O), 140.67 (Ph:Cipso), 128.85, 127,18 (Ph:Cortho,Cmeta), 127.77 (Ph: Cpara), 51.78, 47.18 (CHN), 43.45(CH2CO), 20.65, 19.25 (NCHCH3); m/z (CI) 190 (MH+, 100%), 174(5), 132 (10), 105 (8); (Found: C, 76.02; H, 7.98; 7.07. C12H15NO requires C, 76.16; H, 7.99; N, 7.40%).

Aufarbeitung

  1. customthe reaction was then quenched by addition of pH7 buffer
  2. additionDiethyl ether (20 ml) was added, whereafter the solution
  3. washwas washed with water (20 ml) and brine (20 ml)
  4. dry with materialdried (magnesium sulphate)
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dbc7dc97ba914fc794e8005c19f34ca0
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06037498

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