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(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-one → 5-((R)-2-{2-[4-((S)-2-hydroxy-2-phenylethylamino)phenyl]-ethylamino}-1-(tert-butyldimethylsilanyloxy)ethyl)-8-benzyloxy-1H-quinolin-2-one

HRID 2425506
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Reaktionsgleichung

Reaktionsgleichung von HRID 2425506
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[OH:13])=[CH:6][CH:5]=1.[CH2:20]([O:27][C:28]1[CH:29]=[CH:30][C:31]([C@@H:39]([O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])[CH2:40]Br)=[C:32]2[C:37]=1[NH:36][C:35](=[O:38])[CH:34]=[CH:33]2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CS(C)=O>[OH:13][C@@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:11][NH:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][NH:1][CH2:40][C@@H:39]([C:31]2[CH:30]=[CH:29][C:28]([O:27][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:37]3[C:32]=2[CH:33]=[CH:34][C:35](=[O:38])[NH:36]3)[O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])=[CH:5][CH:6]=1
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Komponenten

4

Edukt 2

HCID 15606253(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-oneHCID 22986856(S)-2-[4-(2-aminoethyl)phenylamino]-1-phenylethanol

Produkt 1

HCID 672471095-((R)-2-{2-[4-((S)-2-hydroxy-2-phenylethylamino)phenyl]-ethylamino}-1-(tert-butyldimethylsilanyloxy)ethyl)-8-benzyloxy-1H-quinolin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl Sulfoxide
Lösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Under nitrogen, (S)-2-[4-(2-aminoethyl)-phenylamino]-1-phenylethanol (1.7 g, 6.6 mmol) and 8-benzyloxy-5-[(R)-2-bromo-1-(tert-butyldimethylsilanyloxy)ethyl]-1H-quinolin-2-one (1.5 g, 3.1 mmol) were treated with dimethyl sulfoxide (4.0 mL) and heated to 120° C. for 40 minutes. The mixture was cooled slowly to room temperature and partitioned between water and ethyl acetate (after removal of some insoluble gummy residue by decantation). The organics were washed with 0.9 M sodium acetate/acetic acid, saturated sodium hydrogen carbonate and saturated sodium chloride, dried over sodium sulfate and evaporated to dryness. The title intermediate was used without further purification.

Aufarbeitung

  1. temperatureThe mixture was cooled slowly to room temperature
  2. custompartitioned between water and ethyl acetate (
  3. customafter removal of some insoluble gummy residue by decantation)
  4. washThe organics were washed with 0.9 M sodium acetate/acetic acid, saturated sodium hydrogen carbonate and saturated sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customThe title intermediate was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-93ef6b169eae49e082d208d93e02d688
Quelldatensatz
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07964730B2

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