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Tetrabutylammonium Fluoride → 4-(4-((R)-(4'-chlorobiphenyl-2-yl)(hydroxy)methyl)piperidin-1-yl)-N-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-nitrophenylsulfonyl)benzamide

HRID 1476351
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1476351
[Si]([O:8][C@@H:9]([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[C:61]1[CH:66]=[CH:65][C:64]([Cl:67])=[CH:63][CH:62]=1)[CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:54]=[CH:53][C:19]([C:20]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][C:29]([NH:32][C@H:33]([CH2:42][CH2:43][N:44]4[CH2:49][CH2:48][O:47][CH2:46][CH2:45]4)[CH2:34][S:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[C:28]([N+:50]([O-:52])=[O:51])[CH:27]=3)(=[O:25])=[O:24])=[O:21])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[Cl:67][C:64]1[CH:65]=[CH:66][C:61]([C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][C:55]=2[C@H:9]([OH:8])[CH:10]2[CH2:11][CH2:12][N:13]([C:16]3[CH:17]=[CH:18][C:19]([C:20]([NH:22][S:23]([C:26]4[CH:31]=[CH:30][C:29]([NH:32][C@H:33]([CH2:42][CH2:43][N:44]5[CH2:45][CH2:46][O:47][CH2:48][CH2:49]5)[CH2:34][S:35][C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)=[C:28]([N+:50]([O-:52])=[O:51])[CH:27]=4)(=[O:25])=[O:24])=[O:21])=[CH:53][CH:54]=3)[CH2:14][CH2:15]2)=[CH:62][CH:63]=1
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Komponenten

3

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 866618754-(4-((R)-(tert-butyldimethylsilyloxy)(4'-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)-N-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-nitrophenylsulfonyl)benzamide2×

Produkt 1

HCID 667237894-(4-((R)-(4'-chlorobiphenyl-2-yl)(hydroxy)methyl)piperidin-1-yl)-N-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-nitrophenylsulfonyl)benzamideAusbeute 79,4 %

Versuchsvorschrift

4-(4-((R)-(tert-butyldimethylsilyloxy)(4′-chlorobiphenyl-2-yl)methyl)piperidin-1-yl)-N-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-nitrophenylsulfonyl)benzamide (INTERMEDIATE 75, 329.0 mg, 0.33 mmol) was charged in a 100 ml flask under nitrogen and treated with TBAF (10.0 ml, 1.0 M in THF, 10 mmol). The resulting solution was stirred at room temperature for 35 minutes whereupon the volatiles were removed under reduced pressure. The concentrate was diluted with DCM (100 ml) and washed with 1N aq. NaHSO4 (100 ml), and saturated aq. NaHCO3 (30 ml), then dried (Na2SO4), filtered, and evaporated under vacuum. The concentrate was purified by column chromatography (ISCO, 12 g silica gel column, eluting with 0→5% MeOH/DCM) followed by further purification by column chromatography (ISCO, 12 g silica gel column, eluting with 0→90% DCM/[10% of 2M NH3 in MeOH/90% DCM]) to provide the title product (228 mg, yield: 78%)

Aufarbeitung

  1. customwere removed under reduced pressure
  2. additionThe concentrate was diluted with DCM (100 ml)
  3. washwashed with 1N aq. NaHSO4 (100 ml), and saturated aq. NaHCO3 (30 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe concentrate was purified by column chromatography (ISCO, 12 g silica gel column, eluting with 0→5% MeOH/DCM)
  8. customfollowed by further purification by column chromatography (ISCO, 12 g silica gel column, eluting with 0→90% DCM/[10% of 2M NH3 in MeOH/90% DCM])

Quellen und Nachweise

ORD-Eintrag
ord-18914a074f464e19bef7bb6555ef0596
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09018381B2

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