Glycidyl benzoate → 2-Hydroxy-3-phenylcarbonyloxypropyl (2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoate

HRID 493369

Reaktionsgleichung

Reaktionsgleichung von HRID 493369
[C:1]([O:9][CH2:10][CH:11]1[CH2:13][O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:14][C:15]1[CH:16]=[C:17]([CH2:22][C@H:23]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:24]([OH:26])=[O:25])[CH:18]=[CH:19][C:20]=1[OH:21]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[OH:14][C:15]1[CH:16]=[C:17]([CH2:22][C@H:23]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:24]([O:26][CH2:13][CH:11]([OH:12])[CH2:10][O:9][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])=[O:25])[CH:18]=[CH:19][C:20]=1[OH:21]

Komponenten

5

Edukt 2

HCID 25998Glycidyl benzoateHCID 14217229N-(tert-Buloxycarbonyl)-3,4-dihydroxy-L-phenylalanine

Produkt 1

HCID 602072522-Hydroxy-3-phenylcarbonyloxypropyl (2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoateAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of oxiran-2-ylmethyl benzoate (3.0 g, 16.8 mmol), (2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoic acid (6.0 g, 20.2 mmol), and tetrabutylammonium bromide (542 mg, 1.7 mmol) in anhydrous toluene was heated to 90° C. for 18 hrs. The reaction mixture was concentrated to dryness under reduced pressure, diluted with ethyl acetate, and washed with water twice followed by the addition of a saturated NaHCO3 solution and brine. The organic layer was dried through MgSO4 and concentrated under reduced pressure. Chromatography (silica gel, 1:1 ethyl acetate/hexane) of the residue afforded 2.05 g (26%) of 2-Hydroxy-3-phenylcarbonyloxypropyl (2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoate.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washwashed with water
  4. additiontwice followed by the addition of a saturated NaHCO3 solution and brine
  5. dry with materialThe organic layer was dried through MgSO4
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-103513a5c7d04c64a75856069b1bb3ae
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534813B2

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