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P-Toluenesulfonamide → 2-acetamido-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide

HRID 892944
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 892944
[C:1]([NH:4][C:5]([CH3:12])([CH:9]([CH3:11])[CH3:10])[C:6]([OH:8])=O)(=[O:3])[CH3:2].C(OC(Cl)=O)C.[CH3:19][C:20]1[CH:21]=[CH:22][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:24][CH:25]=1.[Na]>C(N(CC)CC)C.C(OCC)C.CN(C)C=O>[C:1]([NH:4][C:5]([CH3:12])([CH:9]([CH3:11])[CH3:10])[C:6]([NH:29][S:26]([C:23]1[CH:24]=[CH:25][C:20]([CH3:19])=[CH:21][CH:22]=1)(=[O:27])=[O:28])=[O:8])(=[O:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 6269P-ToluenesulfonamideHCID 10928Ethyl chloroformateHCID 2338052-Acetamido-2,3-dimethylbutanoic acidHCID 5360545Sodium

Produkt 1

HCID 146246882-acetamido-2,3-dimethyl-N-(p-tolylsulfonyl)butyramideAusbeute 116,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283
Diethyl Ether
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel
HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-Acetamido-2,3-dimethylbutyric acid (1.5 g) is dissolved in a solution of triethylamine (2.7 g) in diethyl ether (50 mL) and cooled to 0° C.; ethylchloroformate (1.1 g) is added dropwise and the mixture is stirred at 0° to room temperature over one hour. The mixture is filtered, and the filtrate is concentrated in vacuo to afford the oily mixed anhydride (1.5 g). This material is mixed with 3 g of p-toluenesulfonamide, sodium salt, in 25 mL dimethylformamide, and the resulting mixture is heated at 80° C. for 16 hours. The reaction is cooled, concentrated in vacuo, and the residue is partitioned between methylene chloride and saturated, aqueous sodium bicarbonate. Acidification of the aqueous layer with conc. HCl to pH 1, extraction with CH2Cl2, drying, and stripping the organic phase affords the title product (3.3 g).

Aufarbeitung

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. customto afford the
  4. temperaturethe resulting mixture is heated at 80° C. for 16 hours
  5. temperatureThe reaction is cooled
  6. concentrationconcentrated in vacuo
  7. customthe residue is partitioned between methylene chloride
  8. extractionAcidification of the aqueous layer with conc. HCl to pH 1, extraction with CH2Cl2
  9. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-1aaf1bd93ac045f2967f1539737bd5ad
Quelldatensatz
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05120854

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