Pyridine → N-[4-acetyl-5-(2-methanesulfonylaminoethyl)-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl]-2-phenylpropanamide

HRID 604577

Reaktionsgleichung

Reaktionsgleichung von HRID 604577
[C:1]1([C@@H:7]([CH3:11])[C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1([C@@H](C)C(O)=O)C=CC=CC=1.[C:23]([N:26]1[N:30]=[C:29]([NH2:31])[S:28][C:27]1([CH2:38][CH2:39][NH:40][S:41]([CH3:44])(=[O:43])=[O:42])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:25])[CH3:24].N1C=CC=CC=1>S(Cl)(Cl)=O>[C:23]([N:26]1[C:27]([CH2:38][CH2:39][NH:40][S:41]([CH3:44])(=[O:42])=[O:43])([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[S:28][C:29]([NH:31][C:8](=[O:9])[CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:11])=[N:30]1)(=[O:25])[CH3:24]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 4466262-Phenylpropionic acid, (-)-HCID 7161075(R)-2-phenylpropionyl chlorideHCID 67039184HCID 67039184, Verbindung

Produkt 1

HCID 67039180N-[4-acetyl-5-(2-methanesulfonylaminoethyl)-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl]-2-phenylpropanamideAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

Next, (R)-(−)-2-phenylpropionyl chloride prepared from (R)-(−)-2-phenylpropionic acid (4.65 g, 3.10 mmol) and thionyl chloride (30 mL), and N-[2-(3-acetyl-5-amino-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)ethyl]methane-sulfonamide obtained above were treated in pyridine (5.0 mL, 61.8 mmol) in the same manner as that in Step 1 of Example 20, and the resultant was purified by silica gel column chromatography (chloroform/n-hexane/ethyl acetate/methanol=20/3/2/1) to give one diastereomer of N-[4-acetyl-5-(2-methanesulfonylaminoethyl)-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl]-2-phenylpropanamide (0.75 g, 12%) as a fraction eluted first, and another diastereomer of N-[4-acetyl-5-(2-methane-sulfonylaminoethyl)-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl]-2-phenylpropanamide (0.82 g, 13%) as a fraction eluted later.

Aufarbeitung

  1. customobtained
  2. customthe resultant was purified by silica gel column chromatography (chloroform/n-hexane/ethyl acetate/methanol=20/3/2/1)

Quellen und Nachweise

ORD-Eintrag
ord-095cd61b2e274ae98ade817cc9ffd5c0
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910611B2

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