Hydrochloric Acid → 4-Oxobutyl 1-(4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)-methyl)phenoxy)methyl)benzoyl)piperidine-4-carboxylate

HRID 874812Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 874812
[C:1]1([C@H:7]([NH:41][C:42]([O:44][C@@H:45]2[CH:50]3[CH2:51][CH2:52][N:47]([CH2:48][CH2:49]3)[CH2:46]2)=[O:43])[C:8]2[CH:9]=[C:10]([CH:38]=[CH:39][CH:40]=2)[O:11][CH2:12][C:13]2[CH:37]=[CH:36][C:16]([C:17]([N:19]3[CH2:24][CH2:23][CH:22]([C:25]([O:27][CH2:28][CH2:29][CH2:30][CH:31]4OCC[O:32]4)=[O:26])[CH2:21][CH2:20]3)=[O:18])=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>C1COCC1>[C:1]1([C@H:7]([NH:41][C:42]([O:44][C@@H:45]2[CH:50]3[CH2:49][CH2:48][N:47]([CH2:52][CH2:51]3)[CH2:46]2)=[O:43])[C:8]2[CH:9]=[C:10]([CH:38]=[CH:39][CH:40]=2)[O:11][CH2:12][C:13]2[CH:37]=[CH:36][C:16]([C:17]([N:19]3[CH2:20][CH2:21][CH:22]([C:25]([O:27][CH2:28][CH2:29][CH2:30][CH:31]=[O:32])=[O:26])[CH2:23][CH2:24]3)=[O:18])=[CH:15][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 867223033-(1,3-Dioxolan-2-yl)propyl 1-(4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)-carbonyl)amino)methyl)phenoxy)methyl)benzoyl)piperidine-4-carboxylate

Produkt 1

HCID 867223044-Oxobutyl 1-(4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)-methyl)phenoxy)methyl)benzoyl)piperidine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-(1,3-dioxolan-2-yl)propyl 1-(4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)phenoxy)methyl)benzoyl)piperidine-4-carboxylate in THF (4.7 mL) was added 2 M aqueous hydrochloric acid (4.7 mL). The reaction mixture was stirred at RT for 4 hours. The reaction mixture was partitioned between saturated sodium hydrogen carbonate and ethyl acetate. The organic phase removed and the aqueous phase was extracted with further ethyl acetate (×2). The combined organic phases were washed with brine, dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure. The residue was used directly in the next step with no further purification.

Aufarbeitung

  1. customThe reaction mixture was partitioned between saturated sodium hydrogen carbonate and ethyl acetate
  2. customThe organic phase removed
  3. extractionthe aqueous phase was extracted with further ethyl acetate (×2)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customthe solvent evaporated at reduced pressure
  8. customThe residue was used directly in the next step with no further purification

Quellen und Nachweise

ORD-Eintrag
ord-66cb8d29f4bd4d03ad82223c71b98caf
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980913B2

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