Water → HCID 18977827, compound

HRID 465899Notes

Reaction equation

HRID 465899 reaction equation
[NH:1]([CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].C(N(CC)CC)C.[Br:31][CH2:32][C:33](Br)=[O:34].O>C(Cl)(Cl)(Cl)Cl>[CH2:17]([O:16][C:14]([CH2:13][N:1]([CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])[C:33](=[O:34])[CH2:32][Br:31])=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 10662990HCID 10662990, compound

Product 1

HCID 18977827HCID 18977827, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of dibenzyl iminodiacetate (9.7 g, 0.031 mol) and triethylamine (4.05 g, 0.04 mol) in 30 ml of carbon tetrachloride was added dropwise to a solution of bromoacetyl bromide (8.88 g, 0.044 mol) in 20 ml of carbon tetrachloride at 0° C and stirring was continued for 30 min. After addition of water, the organic layer was washed with saturated-NaHCO3 solution and saturated-brine, dried with MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography [silica gel, hexane:EtOAc (3:1)]and yielded 12.66 g (94%) of Compound 1; NMR (CDCl3): δ 3.86 (s,2H), 4.25 (s,2H), 5.15 (s,2H), 5.19 (s,2H), 7.3-7.5 (m, 10H).

Workup

  1. washthe organic layer was washed with saturated-NaHCO3 solution
  2. dry with materialsaturated-brine, dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography [silica gel, hexane

Sources & evidence

ORD record
ord-471eabd8e20a4e60a6e057d8f7874f97
Source dataset
uspto-grants-1992_10
Patent number
US05154914

Reaction notes

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