4-Amino-3-hydroxybutanoic acid → Methyl 4-[(2,6-dinitrophenyl)amino]-3-hydroxybutanoate

HRID 1628447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628447
[NH2:1][CH2:2][CH:3]([OH:8])[CH2:4][C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH2:13](N(CC)CC)C.Cl[C:21]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[CH:23][C:22]=1[N+:30]([O-:32])=[O:31]>CO.C(OCC)(=O)C.O1CCCC1>[N+:30]([C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([N+:27]([O-:29])=[O:28])[C:21]=1[NH:1][CH2:2][CH:3]([OH:8])[CH2:4][C:5]([O:7][CH3:13])=[O:6])([O-:32])=[O:31]

Komponenten

8

Edukt 4

HCID 21494-Amino-3-hydroxybutanoic acidHCID 8471TriethylamineHCID 118141-Chloro-2,6-dinitrobenzeneHCID 24386Thionyl Chloride

Produkt 1

HCID 86632868Methyl 4-[(2,6-dinitrophenyl)amino]-3-hydroxybutanoateAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of rac-4-amino-3-hydroxybutyric acid (2.00 g, 16.8 mmol) in methanol (40 mL) was added thionyl chloride (1.72 mL, 23.6 mmol) at 0° C. The resultant mixture was stirred at room temperature for 1 hr and concentrated in vacuo. To a mixture of the residue, triethylamine (5.85 mL, 42.0 mmol) and tetrahydrofuran (34 mL) was added 2-chloro-1,3-dinitrobenzene (1.70 g, 8.39 mmol) at room temperature. After the resultant mixture was stirred at 50° C. for 2 hr, the mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound as a yellow solid (2.53 g, 8.45 mmol, quant).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b3145a0841014183a88aeb0ffa2b3408
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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