Triethylamine → 3-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluoro-phenyl}-2-[4-(4-methyl-benzyl)-piperazine-1-sulfonylamino]-propionic acid

HRID 405020

Reaktionsgleichung

Reaktionsgleichung von HRID 405020
C([O:3][C:4](=[O:51])[CH:5]([NH:33][S:34]([N:37]1[CH2:42][CH2:41][N:40]([CH2:43][C:44]2[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=2)[CH2:39][CH2:38]1)(=[O:36])=[O:35])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:20][CH:19]=3)[O:15][N:14]=2)=[C:9]([F:32])[CH:8]=1)C.CC1C=CC(CN2CCNCC2)=CC=1.C(N(CC)CC)C>C(#N)C>[C:28]([O:27][C:25]([NH:24][C:21]1[CH:22]=[CH:23][C:18]([C:16]2[O:15][N:14]=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([CH2:6][CH:5]([NH:33][S:34]([N:37]4[CH2:38][CH2:39][N:40]([CH2:43][C:44]5[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=5)[CH2:41][CH2:42]4)(=[O:35])=[O:36])[C:4]([OH:51])=[O:3])=[CH:8][C:9]=3[F:32])[N:17]=2)=[CH:19][CH:20]=1)=[O:26])([CH3:31])([CH3:30])[CH3:29]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 7647231-(4-Methylbenzyl)piperazineHCID 666312233-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluoro-phenyl}-2-[4-(4-methyl-benzyl)-piperazine-1-sulfonylamino]-propionic acid ethyl ester

Produkt 1

HCID 533745123-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluoro-phenyl}-2-[4-(4-methyl-benzyl)-piperazine-1-sulfonylamino]-propionic acidAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

3-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluoro-phenyl}-2-[4-(4-methyl-benzyl)-piperazine-1-sulfonylamino]-propionic acid ethyl ester. A mixture of oxazolidione from Step A (40 mg, 0.065 mmol), 1-(4-methylbenzyl)piperazine (24.7 mg, 0.13 mmol), and triethylamine (20 mg, 0.2 mmol) in acetonitrile (3 mL) was heated at 85° C. for 2.5 hrs. TLC showed the reaction was completed. The solution was concentrated. Ethyl acetate (20 mL) and 1N aq. HCl solution (10 mL) were added to the solution. The layers were separated, and the aqueous portion was extracted with ethyl acetate (20 mL). The combined organic layer was washed with brine (2×20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound (32 mg, 69% yield) as a yellow solid.

Aufarbeitung

  1. concentrationThe solution was concentrated
  2. additionEthyl acetate (20 mL) and 1N aq. HCl solution (10 mL) were added to the solution
  3. customThe layers were separated
  4. extractionthe aqueous portion was extracted with ethyl acetate (20 mL)
  5. washThe combined organic layer was washed with brine (2×20 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-07a6db3cc0d64055a6f655fdbc806533
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748412B2

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