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Water → Benzyl (2S,3R)-2-(Boc-amino)-3-hydroxy-3-(4-methoxyphenyl)propanoate

HRID 58866
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 58866
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([NH:16][C@@H:17]([C@H:21]([OH:30])[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[C:18]([OH:20])=[O:19])=[O:15])([CH3:12])([CH3:11])[CH3:10].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[C:9]([O:13][C:14]([NH:16][C@@H:17]([C@H:21]([OH:30])[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[C:18]([O:20][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:19])=[O:15])([CH3:12])([CH3:11])[CH3:10]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 14110515(2S,3R)-2-((tert-Butoxycarbonyl)amino)-3-hydroxy-3-(4-methoxyphenyl)propanoic acid

Produkt 1

HCID 131737022Benzyl (2S,3R)-2-(Boc-amino)-3-hydroxy-3-(4-methoxyphenyl)propanoateAusbeute 71,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Benzyl bromide (4.40 g, 25.7 mmol) was added dropwise to a mixture of (2S,3R)-2-(tert-butoxycarbonylamino)-3-hydroxy-3-(4-methoxyphenyl)propanoic acid (4.00 g, 12.9 mmol) and Cs2CO3 (4.20 g, 12.9 mmol) in DMF (80 mL) at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 1 h. Water (80 mL) was added and the resulting mixture was extracted with EtOAc (100 mL×2). The combined extracts were washed with water (100 mL) and brine (100 mL), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=10:1 to 4:1) to afford (2S,3R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-(4-methoxyphenyl)propanoate (3.7 g, 66% yield) as a colorless solid.

Aufarbeitung

  1. extractionthe resulting mixture was extracted with EtOAc (100 mL×2)
  2. washThe combined extracts were washed with water (100 mL) and brine (100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=10:1 to 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-ad1bdf8b1aac4ca799ba93a407c10f0f
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09434761B2

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