Triethylamine → Benzyl 2-(N-((3-(methoxycarbonyl)propen-1-yl) carbonyl)-N-(2-bromophenylmethyl)amino)acetate

HRID 1057476Notes

Reaction equation

HRID 1057476 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH:9][CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].[CH3:21][O:22][C:23](=[O:30])/[CH:24]=[CH:25]/[CH2:26][C:27](O)=[O:28].C(N(CC)CC)C.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1>ClCCl>[CH3:21][O:22][C:23]([CH2:24][CH:25]=[CH:26][C:27]([N:9]([CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])=[O:28])=[O:30]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 18671460Benzyl 2-(N-(2-bromophenylmethyl)amino)acetateHCID 101278073trans-Glutaconic acid methyl ester

Product 1

HCID 69158744Benzyl 2-(N-((3-(methoxycarbonyl)propen-1-yl) carbonyl)-N-(2-bromophenylmethyl)amino)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl 2-(N-(2-bromophenylmethyl)amino)acetate was dissolved in dichloromethane (0.2 M), followed by addition of trans-glutaconic acid methyl ester (1.2 eq), triethylamine (2 eq), EDAC (1.2 eq), and HOAT (0.1 eq). After stirring for 2 hrs, the solution was washed with 10% HCl, 10% sodium carbonate, water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (50% EtOAc/Hex) afforded a viscous oil. EI-MS m/z 460, 462 (M+H)+

Workup

  1. washthe solution was washed with 10% HCl, 10% sodium carbonate, water and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customFlash chromatography (50% EtOAc/Hex) afforded a viscous oil

Sources & evidence

ORD record
ord-5b110cd7f4a94972be42b8bdedc90ccf
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

Loading…