Hydrochloric Acid → HCID 58651194, compound

HRID 1830602Notes

Reaction equation

HRID 1830602 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH2:13][CH2:12]1)=[O:10])(C)(C)C.Cl>C1COCC1>[NH2:7][C@H:8]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[C:9]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH2:15][CH2:16]1)=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58651195HCID 58651195, compound

Product 1

HCID 58651194HCID 58651194, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-{2-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-2-oxo-1-pyridin-2-ylmethyl-ethyl}-carbamic acid tert-butyl ester (3.16 g.; 7.18 mmol from Example 11) in THF (30 mL) at 0° C. was added HCl (4M/Dioxane) (30 mL; 0.12 mol). The mixture was stirred at ambient temperature for 3 hours, and the solvent removed in vacuo. The residue was dissolved in water (35 mL), washed with ether (20 mL). The aqueous layer was rendered basic (pH 9–10) with saturated aqueous Na2CO3, and the product extracted into dichloromethane (3×60 mL). The combined dichloromethane layers were washed with brine, dried over MgSO4, filtered, and the solvent removed in vacuo. The crude residue was purified by flash chromatography on silica gel (5% methanol/chloroform) to afford the free base of the title compound as a light yellow oil (2.07 g.; 85%); MS (+) FAB, [M+H]+ @ m/z 341, [M+Na]+ @ m/z 363; 1H NMR, 400 MHz, DMSO-d6.

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionThe residue was dissolved in water (35 mL)
  3. washwashed with ether (20 mL)
  4. extractionthe product extracted into dichloromethane (3×60 mL)
  5. washThe combined dichloromethane layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customThe crude residue was purified by flash chromatography on silica gel (5% methanol/chloroform)

Sources & evidence

ORD record
ord-c1a952b6f0d642708821738f981519ff
Source dataset
uspto-grants-2006_06
Patent number
US07067518B2

Reaction notes

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