Diisopropylethylamine → Tert-butyl trans-{4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl)cyclohexyl}acetate

HRID 1035699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1035699
[C:1]([O:5][C:6]([CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24]([C:31]1[S:35][C:34]([NH2:36])=[N:33][N:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[CH2:24]([C:31]1[S:35][C:34]([NH:36][C:19]([C:18]2[CH:17]=[CH:16][C:15]([CH:12]3[CH2:13][CH2:14][CH:9]([CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][CH2:11]3)=[CH:23][CH:22]=2)=[O:21])=[N:33][N:32]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 7548235-Benzyl-1,3,4-thiadiazol-2-amineHCID 666854144-(4-Tert-butoxycarbonylmethylcyclohexyl)benzoic acid

Produkt 1

HCID 66739902Tert-butyl trans-{4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl)cyclohexyl}acetateAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

0.45 g of 4-(4-tert-butoxycarbonylmethylcyclohexyl)benzoic acid (1.41 mmol, 1 eq.) is placed in a mixture of 5 mL of dimethylformamide at room temperature. 0.539 g of 5-benzyl-1,3,4-thiadiazol-2-amine (2.82 mmol, 2 eq.), 0.791 g of bromotris-pyrrolidinophosphonium hexafluorophosphonate (1.70 mmol, 1.2 eq.) and 0.49 mL of diisopropylethylamine (2.83 mmol, 2 eq.) are successively added. The reaction mixture is stirred for 16 hours at room temperature, diluted in ethyl acetate and washed three times with water. The organic phase is concentrated. The residue is taken up and washed with ethanol, filtered and dried. 0.236 g of tert-butyl {4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl]cyclohexyl}acetate is obtained.

Aufarbeitung

  1. washwashed three times with water
  2. concentrationThe organic phase is concentrated
  3. washwashed with ethanol
  4. filtrationfiltered
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9f102501a5854ad1bfc91bf51fb59a82
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546391B2

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