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Water → 6-chloro-4'-[5-chloro-2-(1-hydroxycarbonyl-1-propyl-butoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 504590
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 504590
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:45])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([C:31]([O:33]CC)=[O:32])([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27])[CH2:14][C:13](=[O:36])[NH:12][CH:11]3[C:37]3[CH:42]=[C:41]([F:43])[CH:40]=[CH:39][C:38]=3[CH3:44])[C:5]2=[CH:4][CH:3]=1.O[Li].O.O>CO>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:45])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([C:31]([OH:33])=[O:32])([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27])[CH2:14][C:13](=[O:36])[NH:12][CH:11]3[C:37]3[CH:42]=[C:41]([F:43])[CH:40]=[CH:39][C:38]=3[CH3:44])[C:5]2=[CH:4][CH:3]=1
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Komponenten

5

Edukt 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 671438524'-[5-chloro-2-(1-ethoxycarbonyl-1-propyl-butoxy)-phenyl]-6-chloro-2'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Produkt 1

HCID 722961896-chloro-4'-[5-chloro-2-(1-hydroxycarbonyl-1-propyl-butoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneAusbeute 92,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of racemic (2′S,3S,4′R)-6-chloro-4′-[5-chloro-2-(1-ethoxycarbonyl-1-propyl-butoxy)-phenyl]-2′-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (130 mg, 0.198 mmol), LiOH.H2O (1 g, 24.6 mmol), H2O (5 mL) and methanol (15 mL) was refluxed for 2 h. After cooled to room temperature, the solution was concentrated and then the water phase was acidified to “pH” 1-2 by addition of concentrated HCl solution and then extracted with EtOAc. The combined organic layers were washed with water and brine, dried over anhydrous Na2SO4 and concentrated to give the title compound as a light yellow solid (115 mg).

Aufarbeitung

  1. temperaturewas refluxed for 2 h
  2. concentrationthe solution was concentrated
  3. additionby addition of concentrated HCl solution
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a4690528680f40ce92e8ee07f1565fa8
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07776875B2

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