Hydrochloric Acid → N-[(R)-1-[3-(4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-beta-alanine

HRID 1934392Notes

Reaction equation

HRID 1934392 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11](/[CH:14]=[CH:15]/[C:16]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24]([NH:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:25])[CH2:19]2)=[O:17])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[NH:8]1[CH2:9][CH2:10][CH:11](/[CH:14]=[CH:15]/[C:16]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24]([NH:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:25])[CH2:19]2)=[O:17])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70094607N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-beta-alanine

Product 1

HCID 70092913N-[(R)-1-[3-(4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-beta-alanineYield 54.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-β-alanine (1.64 g) in ethyl acetate (16 ml) was added 4N HCl in ethyl acetate (9.37 ml) at 0° C., and the reaction mixture was stirred for 2 hours at room temperature. The precipitates were filtered, washed with ether and resolved in water, neutralized with saturated aqueous NaHCO3, desalted by using the resin of HP-20 eluting with isopropanol-H2O (1:1), then freeze-dried to give N-[(R)-1-[3-(4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-β-alanine as a white powder (690 mg).

Workup

  1. filtrationThe precipitates were filtered
  2. washwashed with ether
  3. washeluting with isopropanol-H2O (1:1)
  4. customfreeze-dried

Sources & evidence

ORD record
ord-64bf493d00154c4d8dd8c8524d49fb2f
Source dataset
uspto-grants-2002_05
Patent number
US06384028B1

Reaction notes

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