Hydrochloric Acid → (S)-methyl 3-((S)-1-phenylethylamino)butanoate

HRID 1637045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637045
[CH3:1][C@H:2]([NH:9][C@@H:10]([CH3:19])[CH2:11][C:12]([O:14][C:15](C)(C)C)=[O:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>CO>[CH3:15][O:14][C:12](=[O:13])[CH2:11][C@@H:10]([NH:9][C@@H:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:19]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 11139971(3S,alphaS)-t-Butyl 3-(alpha-methylbenzylamino)butanoate

Produkt 1

HCID 11096167(S)-methyl 3-((S)-1-phenylethylamino)butanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of compound (29) from Example 14 (1.00 mmol) was stirred in a saturated solution of gaseous hydrogen chloride in methanol for 30 minutes. The solvent was then removed under reduced pressure. This procedure was repeated until no starting material remained. The white solid residue was diluted with ethyl acetate (30 ml), washed with saturated aqueous sodium bicarbonate (2×30 ml), water (20 ml) and brine (20 ml), dried (magnesium sulphate) and filtered, and the solvent was evaporated under reduced pressure to give the title compound (35) as a clear oil. [α]D21 -45.5 (c 1.95, CHCl3); νmax (CHCl3)/cm-1 1736 s (C=O); δH (300 MHz; CDCl3) 7.34-7.20 (5H, m, Ph), 3.88 (1H, q, J=6.5, PhCHCH3), 3.67 (3H, s, OCH3), 2.99 (1H, m, CH3CHCH2), 2.47, 2.38 (2H, ABX system, JAB =14.8, JAX =5.4, JBX =6.5, CH2CO), 1.33 (3H, d, J=6.5 PhCHCH3), 1.06 (3H, d, J=6.4, CH3CHCH2); δC (50 MHz; CDCl3) 173.01 (C=O), 146.29 (Ph:Cipso), 128.63, 126.70 (Ph:Cortho, Cmeta), 127.07 (Ph:Cpara), 55.15, 47.69 (CHN), 51.30 (OCH3), 40.52 (CH2CO), 24.54, 21.34 (NCHCH3); m/z (CI) 222 (MH+, 100%), 206 (15), 148 (10), 118 (5), 105 (10); (Found: C, 70.48; H, 8.80. C13H19NO2 requires C, 70.56; H, 8.65%).

Aufarbeitung

  1. customThe solvent was then removed under reduced pressure
  2. additionThe white solid residue was diluted with ethyl acetate (30 ml)
  3. washwashed with saturated aqueous sodium bicarbonate (2×30 ml), water (20 ml) and brine (20 ml)
  4. dry with materialdried (magnesium sulphate)
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4de34b20a914461782e67151a4944bb6
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06037498

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