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

HRID 874812Notes

Reaction equation

HRID 874812 reaction equation
[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

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-66cb8d29f4bd4d03ad82223c71b98caf
Source dataset
uspto-grants-2015_03
Patent number
US08980913B2

Reaction notes

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