1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Methyl 2-((tert-butoxycarbonyl)amino)prop-2-enoate

HRID 1866839Notes

Reaction equation

HRID 1866839 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C@H:4]([CH2:13]O)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.Cl[Cu]>[CH3:1][O:2][C:3](=[O:15])[C:4]([NH:5][C:6]([O:8][C:9]([CH3:11])([CH3:10])[CH3:12])=[O:7])=[CH2:13]

Participants

5

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7019177N-Boc-L-serine methyl ester2×

Product 1

HCID 10932500Methyl 2-((tert-butoxycarbonyl)amino)prop-2-enoate

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-Boc-serine methyl ester (Compound 1e, 2.19 g, 10 mmol) and EDCl (2.01 g, 10.5 mmol) in DCM (70 mL) was added CuCl (1.04 g, 10.5 mmol). The reaction mixture was stirred at room temperature for 72 h. Upon removal of the solvent, the residue was diluted with EtOAc, washed sequentially with water and brine and then dried over MgSO4. The crude product was purified by flash column chromatography (eluent: EtOAc:hexane ˜1:4) to yield compound if as a colorless oil.

Workup

  1. customUpon removal of the solvent
  2. additionthe residue was diluted with EtOAc
  3. washwashed sequentially with water and brine
  4. dry with materialdried over MgSO4
  5. customThe crude product was purified by flash column chromatography (eluent: EtOAc:hexane ˜1:4)
  6. customto yield compound if as a colorless oil

Sources & evidence

ORD record
ord-f9e0d70f048c428da51a21eb3f8e43ed
Source dataset
uspto-grants-2009_12
Patent number
US07629488B2

Reaction notes

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