Benzyl {6-[(2-{4-[(biphenyl-2-ylcarbamoyl)oxy]piperidin-1-yl}ethyl)(methyl)amino]-6-oxohexyl}(4-{[N-({[(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)-N-methyl-beta-alanyl](methyl)amino}phenyl)carbamate → 1-{2-[{6-[(4-{[N-({[(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)-N-methyl-beta-alanyl](methyl)amino}phenyl)amino]hexanoyl}(methyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamate

HRID 446613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446613
[C:1]1([C:101]2[CH:106]=[CH:105][CH:104]=[CH:103][CH:102]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([O:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]([CH3:100])[C:20](=[O:99])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([C:37]2[CH:42]=[CH:41][C:40]([N:43]([C:45](=[O:98])[CH2:46][CH2:47][N:48]([C:50](=[O:97])[CH2:51][O:52][C@@H:53]3[C:61]4([CH2:66][CH2:65][N:64]([CH2:67][CH2:68][C@:69]5([C:90]6[CH:95]=[CH:94][C:93]([F:96])=[CH:92][CH:91]=6)[O:73][CH2:72][N:71]([C:74](=[O:89])[C:75]6[CH:80]=[C:79]([C:81]([F:84])([F:83])[F:82])[CH:78]=[C:77]([C:85]([F:88])([F:87])[F:86])[CH:76]=6)[CH2:70]5)[CH2:63][CH2:62]4)[C:60]4[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=4)[CH2:54]3)[CH3:49])[CH3:44])=[CH:39][CH:38]=2)C(=O)OCC2C=CC=CC=2)[CH2:13][CH2:12]1)=[O:9]>C(O)C.C(OCC)(=O)C.[C].[Pd]>[C:1]1([C:101]2[CH:102]=[CH:103][CH:104]=[CH:105][CH:106]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:9])[O:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]([C:20](=[O:99])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:37]2[CH:38]=[CH:39][C:40]([N:43]([C:45](=[O:98])[CH2:46][CH2:47][N:48]([C:50](=[O:97])[CH2:51][O:52][C@@H:53]3[C:61]4([CH2:66][CH2:65][N:64]([CH2:67][CH2:68][C@:69]5([C:90]6[CH:95]=[CH:94][C:93]([F:96])=[CH:92][CH:91]=6)[O:73][CH2:72][N:71]([C:74](=[O:89])[C:75]6[CH:80]=[C:79]([C:81]([F:82])([F:83])[F:84])[CH:78]=[C:77]([C:85]([F:87])([F:88])[F:86])[CH:76]=6)[CH2:70]5)[CH2:63][CH2:62]4)[C:60]4[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=4)[CH2:54]3)[CH3:49])[CH3:44])=[CH:41][CH:42]=2)[CH3:100])[CH2:13][CH2:12]1

Komponenten

5

Edukt 1

HCID 86663479Benzyl {6-[(2-{4-[(biphenyl-2-ylcarbamoyl)oxy]piperidin-1-yl}ethyl)(methyl)amino]-6-oxohexyl}(4-{[N-({[(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)-N-methyl-beta-alanyl](methyl)amino}phenyl)carbamate

Produkt 1

HCID 867619211-{2-[{6-[(4-{[N-({[(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)-N-methyl-beta-alanyl](methyl)amino}phenyl)amino]hexanoyl}(methyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamateAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The compound (180 mg, 0.12 mmol) obtained in Example 97f was dissolved in a mixed solvent of ethanol (3 mL) and ethyl acetate (3 mL), 10% palladium-carbon (36 mg, 20% by weight) was added, and the mixture was stirred at room temperature under a hydrogen atmosphere for 18 hours. After the reaction was completed, the reaction mixture was filtered through celite, the filtrate was washed with methanol, and the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:methanol, 30:1, v/v) to give the title compound (141 mg; yield, 86%) as a white solid.

Aufarbeitung

  1. additionwas added
  2. filtrationthe reaction mixture was filtered through celite
  3. washthe filtrate was washed with methanol
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography (ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c17ffaa0fa5b44fb8252057e642e87f3
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476253B2

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