Hydrochloric Acid → HCID 86720831, compound

HRID 877330Notes

Reaction equation

HRID 877330 reaction equation
[C:1]1([C@H:7]([NH:24][C:25]([O:27][C@@H:28]2[CH:33]3[CH2:34][CH2:35][N:30]([CH2:31][CH2:32]3)[CH2:29]2)=[O:26])[C:8]2[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=2)[O:11][CH2:12][C:13]2[O:17][C:16]([C:18]([OH:20])=[O:19])=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)=O.C1([C@H](NC(O[C@@H]2C3CCN(CC3)C2)=O)C2C=C(C=CC=2)OCC2OC(C(O)=O)=CC=2)C=CC=CC=1.[ClH:74].CCOCC>O1CCOCC1>[ClH:74].[C:1]1([C@H:7]([NH:24][C:25]([O:27][C@@H:28]2[CH:33]3[CH2:34][CH2:35][N:30]([CH2:31][CH2:32]3)[CH2:29]2)=[O:26])[C:8]2[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=2)[O:11][CH2:12][C:13]2[O:17][C:16]([C:18]([OH:20])=[O:19])=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86720832HCID 86720832, compoundHCID 86720833HCID 86720833, compound

Product 1

HCID 86720831HCID 86720831, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

The 5-((3-((S)-phenyl(((R)-quinuclidin-3-yloxy)carbonylamino)methyl)phenoxy)-methyl)furan-2-carboxylic acid prepared as described in Example 6 Step 1 was further purified by reverse phase column chromatography eluting with gradient of Eluent A: Water/ACN 95/5+0.1% HCOOH and Eluent B: ACN/water 95/5+0.1% HCOOH. 5-((3-((S)-phenyl(((R)-quinuclidin-3-yloxy)carbonylamino)methyl)phenoxy)methyl)furan-2-carboxylic acid formate (1:1) (8.36 g, 16.12 mmol) was dispersed in Dioxane (50 mL) and then 4M HCl in dioxane (16.12 mL, 64.5 mmol) was added at 0° C. and the mixture stirred at rt for 10 minutes until complete dissolution. The above mentioned solution was dropped in a 500 mL of Et2O under vigorous stirring to give a white precipitate that was collected by filtration. After drying under vacuum 5-((3-((S)-phenyl(((R)-quinuclidin-3-yloxy)carbonylamino)methyl)phenoxy)methyl)furan-2-carboxylic acid hydrochloride (8.2 g, 15.98 mmol, 99% yield) was isolate as a white solid.

Workup

  1. customwas further purified by reverse phase column chromatography
  2. washeluting with gradient of Eluent A
  3. stirringunder vigorous stirring
  4. customto give a white precipitate that
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-02e8d9190f094f42aa9a54ed43456fcf
Source dataset
uspto-grants-2015_03
Patent number
US08987299B2

Reaction notes

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