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

HRID 1934391Notes

Reaction equation

HRID 1934391 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH2:5][CH2:6][NH:7][C:8]([C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16](=[O:32])/[CH:17]=[CH:18]/[CH:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)[CH2:11]1)=[O:9])[CH3:2].Cl>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:33])[CH2:5][CH2:6][NH:7][C:8]([C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16](=[O:32])/[CH:17]=[CH:18]/[CH:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)[CH2:11]1)=[O:9])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70093214N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-beta-alanine ethyl ester

Product 1

HCID 70096899N-[(R)-1-[3-(4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-beta-alanine ethyl esterYield 72.9%

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 ethyl ester (0.8 g) in ethyl acetate (8 ml) was added 4N HCl in ethyl acetate (4.3 ml) at 0° C., and the reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was concentrated in vacuo, 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 ethyl ester (458 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washeluting with isopropanol-H2O (1:1)
  3. customfreeze-dried

Sources & evidence

ORD record
ord-a3ae5f94f33040e78b10b9e2e4a64826
Source dataset
uspto-grants-2002_05
Patent number
US06384028B1

Reaction notes

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