(R)-3-(2-(2-(tert-Butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)-2-methylpropyl)benzaldehyde → (R)-5-(1-(tert-Butyldimethylsilyloxy)-2-(1-(3-((4-(5-isopropylthiophene-3-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)-2-methylpropan-2-ylamino)ethyl)-8-hydroxyquinolin-2(1H)-one

HRID 1689520Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689520
[Si:1]([O:8][C@H:9]([C:24]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]2[C:25]=1[CH:26]=[CH:27][C:28](=[O:35])[NH:29]2)[CH2:10][NH:11][C:12]([CH3:23])([CH3:22])[CH2:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:36]([C:39]1[S:43][CH:42]=[C:41]([C:44]([N:46]2[CH2:51][C:50]3([CH2:56][CH2:55][NH:54][CH2:53][CH2:52]3)[O:49][CH2:48][CH2:47]2)=[O:45])[CH:40]=1)([CH3:38])[CH3:37]>>[Si:1]([O:8][C@H:9]([C:24]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]2[C:25]=1[CH:26]=[CH:27][C:28](=[O:35])[NH:29]2)[CH2:10][NH:11][C:12]([CH3:23])([CH3:22])[CH2:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:16]([CH2:17][N:54]2[CH2:53][CH2:52][C:50]3([O:49][CH2:48][CH2:47][N:46]([C:44]([C:41]4[CH:40]=[C:39]([CH:36]([CH3:38])[CH3:37])[S:43][CH:42]=4)=[O:45])[CH2:51]3)[CH2:56][CH2:55]2)[CH:15]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Komponenten

3

Edukt 2

HCID 57989117(R)-3-(2-(2-(tert-Butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)-2-methylpropyl)benzaldehydeHCID 57989215(5-Isopropylthiophen-3-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

Produkt 1

HCID 57989329(R)-5-(1-(tert-Butyldimethylsilyloxy)-2-(1-(3-((4-(5-isopropylthiophene-3-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)-2-methylpropan-2-ylamino)ethyl)-8-hydroxyquinolin-2(1H)-one

Versuchsvorschrift

The subtitled compound was prepared using a similar method to that described in Example 14, step b) using (R)-3-(2-(2-(tert-butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)-2-methylpropyl)benzaldehyde (0.32 g) (Example 275, step h) and (5-isopropylthiophen-3-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone (0.21 g) (Example 275, step i)). The crude product was purified by flash silica chromatography, 8% methanol in dichloromethane with 1% 880 aqueous ammonia. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.31 g.

Aufarbeitung

  1. customThe subtitled compound was prepared
  2. customThe crude product was purified by flash silica chromatography, 8% methanol in dichloromethane with 1% 880 aqueous ammonia
  3. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-22a6b90aebaa42928e721393ba23597e
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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