Hydrochloric Acid → HCID 46938190, compound

HRID 1873707Notes

Reaction equation

HRID 1873707 reaction equation
C([N:8]1[CH2:13][C@@H:12]([CH2:14][F:15])[C@:11](OCC2C=CC=CC=2)([OH:16])[C@H:10]([O:25]CC2C=CC=CC=2)[CH2:9]1)C1C=CC=CC=1.[ClH:33]>CCO>[ClH:33].[F:15][CH2:14][C@@H:12]1[CH2:13][NH:8][CH2:9][C@@H:10]([OH:25])[C@@H:11]1[OH:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66738030HCID 66738030, compound

Product 1

HCID 46938190HCID 46938190, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5 (0.24 g, 0.57 mmol) in EtOH (40 mL) was added 0.5 mL of 6N HCl in 2-PrOH. The solvent was evaporated in vacuo and then co-evaporated 2× more with EtOH. The residue was dissolved in EtOH and hydrogenated at 55 psi using Pd(OH)2 as catalyst. After 14 hrs the starting material could no longer be detected and the solution was filtered and the filtrate was evaporated in vacuo. The residue was triturated with acetone and then filtered to give an off white solid (0.09 g, 85%) as the title compound. 1H NMR (DMSO-d6) 1.95-2.05 (m, 1H), 2.65 (t, 1H), 2.85 (t, 1H) 3.15-3.4 (m, 3H), 3.55 (m, 1H), 4.55 (m, 1H), 4.65 (m, 1H), 5.45-5.6 (dd, 2H), 9.05 (br s, 2H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in EtOH and hydrogenated at 55 psi
  3. filtrationthe solution was filtered
  4. customthe filtrate was evaporated in vacuo
  5. customThe residue was triturated with acetone
  6. filtrationfiltered

Sources & evidence

ORD record
ord-a603dd1bc9ec4c1092f5759d08285e11
Source dataset
uspto-grants-2012_11
Patent number
US08304429B2

Reaction notes

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