Water → HCID 54036883, compound

HRID 1680505Notes

Reaction equation

HRID 1680505 reaction equation
[CH3:1][C:2]([CH3:11])([O:4][C:5]([NH:7][CH2:8][CH2:9][NH2:10])=[O:6])[CH3:3].[CH3:12][O:13][C:14](=[O:28])[CH:15](Br)[C:16]1[C:17]([CH:22](Br)[C:23]([OH:25])=[O:24])=[CH:18][CH:19]=[CH:20][CH:21]=1.[CH2:29](N(CC)CC)C.O>C1C=CC=CC=1>[CH3:12][O:13][C:14]([CH:15]1[C:16]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:22]([C:23]([O:25][CH3:29])=[O:24])[N:10]1[CH2:9][CH2:8][NH:7][C:5]([O:4][C:2]([CH3:11])([CH3:1])[CH3:3])=[O:6])=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 187201N-BOC-ethylenediamineHCID 54556282HCID 54556282, compound

Product 1

HCID 54036883HCID 54036883, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of N-(1,1-dimethylethoxycarbonyl)-ethylene diamine (3 g) in benzene (25 ml) is added dropwise to a solution of α,α'-dibromo-1,2-benzenediacetic acid methyl ester (3.78 g) and triethylamine (3.5 g) in benzene (75 ml). The mixture is refluxed for 18 hr using a water separator condenser and filtered. The filtrate is evaporated and the residue is chromatographed on silica gel using diethyl ether-hexane-pyridine (500:500:1). The eluate is evaporated to give the title compound (1.7 g), nmr (CDCl3) δ1.4(s), 3.03(m), 3.63(s), 5.0(s) and 7.17(m).

Workup

  1. temperatureThe mixture is refluxed for 18 hr
  2. filtrationfiltered
  3. customThe filtrate is evaporated
  4. customthe residue is chromatographed on silica gel
  5. customThe eluate is evaporated

Sources & evidence

ORD record
ord-1c98f54ebf9e42cdbe903ba891a01bba
Source dataset
uspto-grants-1981_06
Patent number
US04273773

Reaction notes

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