Hydrochloric Acid → HCID 69458122, compound

HRID 1351978Notes

Reaction equation

HRID 1351978 reaction equation
[OH:1][C@H:2]([C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[CH2:3][NH:4][C@H:5]([CH3:22])[CH2:6][C:7]1[C:15]2[C:10](=[C:11]([O:16][C@@H:17]([CH3:21])[C:18]([OH:20])=[O:19])[CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1.Cl.[C:30](OCC)(=O)[CH3:31].C(OC(C)C)(C)C>C(O)C.O1CCOCC1>[OH:1][C@H:2]([C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[CH2:3][NH:4][C@H:5]([CH3:22])[CH2:6][C:7]1[C:15]2[C:10](=[C:11]([O:16][C@@H:17]([CH3:21])[C:18]([O:20][CH2:30][CH3:31])=[O:19])[CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 8857Ethyl AcetateHCID 69460032HCID 69460032, compound

Product 1

HCID 69458122HCID 69458122, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of (2S)-2-((3-((2R)-2-(((2R)-2-hydroxy-2-pyridin-3-ylethyl)amino)propyl)-1H-indol-7-yl)oxy)propanoic acid (6.72 g, 17.53 mmol) in ethanol (135 mL) is added a 4N solution of hydrogen chloride in dioxane (55 mL), and the mixture is stirred at room temperature for 2 hours. The reaction solution is evaporated to remove the solvent, and the residue is separated into a saturated aqueous sodium hydrogen carbonate solution and chloroform. The organic layer is washed with a saturated brine, and dried over anhydrous sodium sulfate. The mixture is evaporated to remove the solvent, and to the obtained crude product are added ethyl acetate (50 mL) and diisopropyl ether (50 mL). The product is crystallized and collected by filtration. The product on the filter is washed with diisopropyl ether, and dried to give the title compound (6.26 g, yield: 87%).

Workup

  1. customThe reaction solution is evaporated
  2. customto remove the solvent
  3. customthe residue is separated into a saturated aqueous sodium hydrogen carbonate solution and chloroform
  4. washThe organic layer is washed with a saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe mixture is evaporated
  7. customto remove the solvent
  8. customto the obtained crude product
  9. customThe product is crystallized
  10. filtrationcollected by filtration
  11. washThe product on the filter is washed with diisopropyl ether
  12. customdried

Sources & evidence

ORD record
ord-e7f314346d0f4e2a9f24ffd108afb759
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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