Sodium Bicarbonate → [10-(4-Chlorophenyl)-8-(2,2-difluoroethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone

HRID 73016

Reaktionsgleichung

Reaktionsgleichung von HRID 73016
FC(F)(F)S(O[CH2:7][CH:8]([F:10])[F:9])(=O)=O.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[O:43][C:24]3([CH2:29][CH2:28][N:27]([C:30]([C:32]4[CH:37]=[CH:36][C:35]([O:38][CH:39]([CH3:41])[CH3:40])=[C:34]([CH3:42])[CH:33]=4)=[O:31])[CH2:26][CH2:25]3)[CH2:23][NH:22][CH2:21]2)=[CH:16][CH:15]=1.C([O-])(O)=O.[Na+]>C(O)C>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[O:43][C:24]3([CH2:25][CH2:26][N:27]([C:30]([C:32]4[CH:37]=[CH:36][C:35]([O:38][CH:39]([CH3:40])[CH3:41])=[C:34]([CH3:42])[CH:33]=4)=[O:31])[CH2:28][CH2:29]3)[CH2:23][N:22]([CH2:7][CH:8]([F:10])[F:9])[CH2:21]2)=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 70872702[10-(4-Chlorophenyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone

Produkt 1

HCID 86672477[10-(4-Chlorophenyl)-8-(2,2-difluoroethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanoneAusbeute 106,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

2,2-difluoroethyl trifluoromethanesulfonate (17 mg, 0.08 mmol) was added to a solution of [10-(4-chlorophenyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (22 mg, 0.05 mmol) and NaHCO3 (13 mg, 0.15 mmol) in anhydrous ethanol (0.3 mL) at room temperature. The reaction mixture was purged with argon, sealed with a cap and heated at 70° C. for 40 minutes. The reaction mixture was cooled to room temperature, diluted with MeOH to 1 mL, microfiltered and purified by Waters mass directed LC/MS: (10-99% ACN/H2O (5 mM HCl)) to yield [10-(4-chlorophenyl)-8-(2,2-difluoroethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (27 mg, 100%). ESI-MS m/z calc. 506.21478. Found 507.2 (M+1)+; Retention time: 2.17 minutes (3 min run).

Aufarbeitung

  1. customThe reaction mixture was purged with argon
  2. customsealed with
  3. customa cap
  4. temperatureThe reaction mixture was cooled to room temperature
  5. additiondiluted with MeOH to 1 mL
  6. custommicrofiltered and purified by Waters mass

Quellen und Nachweise

ORD-Eintrag
ord-13e8da07d543418abb593c868fbb31a8
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828996B2

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