Hydrochloric Acid → HCID 86720822, compound

HRID 2205700Notes

Reaction equation

HRID 2205700 reaction equation
[C:1]1([C@H:7]([NH:37][C:38]([O:40][C@@H:41]2[CH:46]3[CH2:47][CH2:48][N:43]([CH2:44][CH2:45]3)[CH2:42]2)=[O:39])[C:8]2[CH:9]=[C:10]([CH:34]=[CH:35][CH:36]=2)[O:11][CH2:12][C:13]2[CH:33]=[CH:32][C:16]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]4OCC[O:28]4)[CH:22]=3)=[O:18])=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>C1COCC1.C(OCC)(=O)C>[C:1]1([C@H:7]([NH:37][C:38]([O:40][C@@H:41]2[CH:46]3[CH2:47][CH2:48][N:43]([CH2:44][CH2:45]3)[CH2:42]2)=[O:39])[C:8]2[CH:9]=[C:10]([CH:34]=[CH:35][CH:36]=2)[O:11][CH2:12][C:13]2[CH:33]=[CH:32][C:16]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=[O:28])[CH:22]=3)=[O:18])=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86720823HCID 86720823, compound

Product 1

HCID 86720822HCID 86720822, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3-(1,3-dioxolan-2-yl)benzyl 4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)phenoxy)methyl)benzoate (0.32 g, 0.57 mmol) in THF (8 mL) was added 2M aqueous hydrochloric acid (8 mL). The reaction mixture was stirred at RT for 1 hour. The mixture was diluted with ethyl acetate and was washed sequentially with saturated aqueous sodium hydrogen carbonate and brine. The organic extract was dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure. The residue was used in the next step with no further purification.

Workup

  1. washwas washed sequentially with saturated aqueous sodium hydrogen carbonate and brine
  2. extractionThe organic extract
  3. dry with materialwas dried (magnesium sulfate)
  4. filtrationfiltered
  5. customthe solvent evaporated at reduced pressure
  6. customThe residue was used in the next step with no further purification

Sources & evidence

ORD record
ord-93954b77c57645d1997ed98b2ef130c6
Source dataset
uspto-grants-2016_06
Patent number
US09371318B2

Reaction notes

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