Cyclopentylamine → (E)-Ethyl 2-acetamido-3-(cyclopentylamino)but-2-enoate

HRID 75495

Reaction equation

HRID 75495 reaction equation
[C:1]([NH:4]/[C:5](=[C:11](/[N:13]([CH3:15])C)\[CH3:12])/[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[CH:16]1(N)[CH2:20]C[CH2:18][CH2:17]1>CC(O)=O.O>[C:1]([NH:4]/[C:5](=[C:11](/[NH:13][CH:15]1[CH2:18][CH2:17][CH2:16][CH2:20]1)\[CH3:12])/[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 2906CyclopentylamineHCID 54579441(E)-ethyl 2-acetamido-3-(dimethylamino)but-2-enoate2×

Product 1

HCID 54579442(E)-Ethyl 2-acetamido-3-(cyclopentylamino)but-2-enoate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

(E)-ethyl 2-acetamido-3-(dimethylamino)but-2-enoate (compound 16, 1 g, 4.67 mmol) and cyclopentylamine (0.5 mL) were stirred at room temperature in AcOH (10 mL) for overnight. The reaction mixture was diluted slowly with water (10 mL) and evaporated under reduced pressure to obtain the desired product as a dark brown oil, which could be used without any further purification for the next step.

Workup

  1. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f21a1bee4a0f4c51879b70c98fcafeea
Source dataset
uspto-grants-2014_09
Patent number
US08835436B2

Linked notes

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