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Lithium Hydroxide → Rac-2-(4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclopentanecarboxylic acid

HRID 557761
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 557761
C([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:28]3[N:29]=[C:30]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[O:31][C:32]=3[C:33]([F:36])([F:35])[F:34])=[O:27])=[CH:21][CH:20]=2)[CH2:15][CH2:14]1)=[O:12])=[O:5])C.[OH-].[Li+]>C(O)C.O>[C:37]1([C:30]2[O:31][C:32]([C:33]([F:34])([F:35])[F:36])=[C:28]([C:26]([NH:25][C:22]3[CH:23]=[CH:24][C:19]([N:16]4[CH2:17][CH2:18][N:13]([C:11]([CH:7]5[CH2:8][CH2:9][CH2:10][CH:6]5[C:4]([OH:5])=[O:3])=[O:12])[CH2:14][CH2:15]4)=[CH:20][CH:21]=3)=[O:27])[N:29]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1
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Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 66738241Rac-2-(4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclopentanecarboxylic acid ethyl ester

Produkt 1

HCID 66738247Rac-2-(4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclopentanecarboxylic acidAusbeute 28,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702
Ethanol
Lösungsmittel
HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of racemic 2-(4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclopentanecarboxylic acid ethyl ester (100 mg, 0.171 mmol) in 10 mL ethanol was added a solution of lithium hydroxide (14 mg, 0.342 mmol) in 5 mL water. The reaction mixture was stirred at room temperature for 4 hrs and then heated to 50° C. for 1 hr. The reaction mixture was cooled, diluted with water, and washed with diethyl ether. The pH of the aqueous layer was adjusted to pH 5 with 1N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layers were dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography (eluted with ethyl acetate/methylene chloride) to yield rac-2-(4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclopentanecarboxylic acid (27 mg, 28%). ES-MS calcd for C28H27F3N4O5 (m/e) 556.54, obsd 557.1 (M+H).

Aufarbeitung

  1. temperatureheated to 50° C. for 1 hr
  2. temperatureThe reaction mixture was cooled
  3. washwashed with diethyl ether
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by flash chromatography (eluted with ethyl acetate/methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-5c76505f5be847b5b488ad9b23416da8
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08058299B2

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