1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-2-methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-benzoic acid ethyl ester

HRID 1269523

Reaktionsgleichung

Reaktionsgleichung von HRID 1269523
[NH:1]1[CH2:6][CH2:5][CH2:4][C@H:3]([C:7]2[CH:8]=[CH:9][C:10]([CH3:18])=[C:11]([CH:17]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:2]1.C(O)(=O)[C@H]([C@@H](C(O)=O)O)O.CN(C)CCCN=C=NCC.[CH3:40][C:41]1[N:42]=[C:43]([C:49]2[CH:54]=[CH:53][C:52]([C:55]([F:58])([F:57])[F:56])=[CH:51][CH:50]=2)[S:44][C:45]=1[C:46](O)=[O:47]>C(OCC)(=O)C.C(OCC)C>[CH2:15]([O:14][C:12](=[O:13])[C:11]1[CH:17]=[C:7]([C@H:3]2[CH2:4][CH2:5][CH2:6][N:1]([C:46]([C:45]3[S:44][C:43]([C:49]4[CH:50]=[CH:51][C:52]([C:55]([F:58])([F:56])[F:57])=[CH:53][CH:54]=4)=[N:42][C:41]=3[CH3:40])=[O:47])[CH2:2]2)[CH:8]=[CH:9][C:10]=1[CH3:18])[CH3:16]

Komponenten

6

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27756634-Methyl-2-(4-(trifluoromethyl)phenyl)-5-thiazolecarboxylic acidHCID 86593890(R)-Ethyl 5-(3-piperidinyl)-2-methylbenzoate D-tartaric acid

Produkt 1

HCID 68884364(R)-2-methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-benzoic acid ethyl esterAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(R)-ethyl 5-(3-piperidinyl)-2-methylbenzoate-D-tartaric acid (Example 9; 2.13 g, 5.36 mmol) was dissolved in 100 mL ethyl acetate and washed with 100 mL saturated aqueous NaHCO3. The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The resultant oil was taken up in 20 mL CH2Cl2 and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide (2.05 g, 10.72 mmol) and 4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylic acid (1.69 g, 5.90 mmol) were added. The reaction was stirred at ambient temperature under nitrogen for 72 h. The reaction was diluted with 200 mL diethyl ether and washed with water (100 mL), saturated aqueous NaHCO3 (2×100 mL), 0.5 N HCl (2×100 mL), water (100 mL), and brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure to yield (R)-2-methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-benzoic acid ethyl ester (2.62 g, 95%) as a clear oil.

Aufarbeitung

  1. washwashed with 100 mL saturated aqueous NaHCO3
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. washwashed with water (100 mL), saturated aqueous NaHCO3 (2×100 mL), 0.5 N HCl (2×100 mL), water (100 mL), and brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ff97ce2658424a27917911feb5df6ead
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199243B2

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