Triethylamine → Ethyl 7-[({[(2S)-1'-{2-[(5R)-3-[3,5-bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]heptanoate

HRID 446562Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446562
[F:1][C:2]([F:49])([F:48])[C:3]1[CH:4]=[C:5]([CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:43]=1)[C:6]([N:8]1[CH2:12][C@@:11]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][C:25]3([C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:29][C@@H:28]3[O:36]CC(O)=O)[CH2:24][CH2:23]2)([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:10][CH2:9]1)=[O:7].[CH2:50]([N:52]([CH2:55][CH3:56])[CH2:53][CH3:54])C.ClC(OCC(C)C)=[O:59].CNCC[CH2:69][CH2:70][CH2:71][CH2:72][C:73]([O:75][CH2:76][CH3:77])=[O:74].C(=O)([O-])O.[Na+]>ClCCl>[F:47][C:44]([F:45])([F:46])[C:42]1[CH:41]=[C:5]([CH:4]=[C:3]([C:2]([F:49])([F:48])[F:1])[CH:43]=1)[C:6]([N:8]1[CH2:12][C@@:11]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][C:25]3([C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:29][C@@H:28]3[O:36][CH2:54][C:53]([N:52]([CH3:50])[CH2:55][CH2:56][CH2:69][CH2:70][CH2:71][CH2:72][C:73]([O:75][CH2:76][CH3:77])=[O:74])=[O:59])[CH2:24][CH2:23]2)([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:10][CH2:9]1)=[O:7]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 86663420{[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetic acidHCID 86663458Ethyl 7-(methylamino)heptanoate

Produkt 1

HCID 86663457Ethyl 7-[({[(2S)-1'-{2-[(5R)-3-[3,5-bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]heptanoateAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The compound (625 mg, 0.901 mmol) obtained in Example 1j was dissolved in dichloromethane (9 mL), triethylamine (0.376 mL, 2.70 mmol) and isobutyl chloroformate (183 μL, 1.35 mmol) were added under ice cooling, and the mixture was stirred at the same temperature. The compound (467 mg, 2.70 mmol) obtained in Example 68a was added under ice cooling, and then the temperature was increased to room temperature. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with dichloromethane (×2). The resulting organic layer was dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by NH silica gel column chromatography (a elution solvent, ethyl acetate) to give the title compound (615 mg; yield, 79%).

Aufarbeitung

  1. extractionthe mixture was extracted with dichloromethane (×2)
  2. dry with materialThe resulting organic layer was dried with anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by NH silica gel column chromatography (a elution solvent, ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-df1a81ab01114d1293e99b34a2462de2
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476253B2

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