4-Pentenoic acid → HCID 86635052, compound

HRID 1924377Notes

Reaction equation

HRID 1924377 reaction equation
[C:1]([OH:7])(=O)[CH2:2][CH2:3][CH:4]=[CH2:5].[C:8]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:11])[NH:9][NH2:10].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[C:1]([NH:10][NH:9][C:8]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(=[O:7])[CH2:2][CH2:3][CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 611384-Pentenoic acidHCID 70091tert-Butyl carbazateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86635052HCID 86635052, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of pent-4-enoic acid 0.1 M in DCM, tert-butyl carbazate (2 eq) was added followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.02 eq) and the mixture was allowed to stir at RT overnight. DCM was added and the organic solution was washed sequentially with saturated aq. NaHCO3 followed by saturated aq. NaCl and then dried over Na2SO4. Removal of the solvent in vacuo yielded the title compound as colorless oil. This material was used in the next step without further purification. 1H NMR (300 MHz, DMSO-d6) δ: 7.33 (bs, 1H), 6.51 (bs, 1H), 5.88-5.75 (m, 1H), 5.10-4.99 (m, 2H), 2.43-2.38 (m, 2H), 2.32 (t, J 6.8, 2H), 2.03 (s, 9H).

Workup

  1. washthe organic solution was washed sequentially with saturated aq. NaHCO3
  2. dry with materialdried over Na2SO4
  3. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-6643b0b2b42848e68b096117522f9c6d
Source dataset
uspto-grants-2012_05
Patent number
US08178520B2

Reaction notes

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