1,2-Dichloroethane → HCID 15850761, compound

HRID 583672Notes

Reaction equation

HRID 583672 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])([OH:3])=O.[C:14]([NH:21][CH2:22][CH2:23][NH2:24])([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.C(Cl)CCl>CN(C=O)C>[C:14]([NH:21][CH2:22][CH2:23][NH:24][C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])=[O:3])([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 187201N-BOC-ethylenediamineHCID 6018803-(Methoxycarbonyl)benzoic acid

Product 1

HCID 15850761HCID 15850761, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 3-carboxybenzoate (16-3) (Aldrich) (0.9 g, 5 mmol), 16-2 (0.8 g, 5 mmol), and HOBT (0.74 g, 5.5 mmol) in DMF (20 ml) was treated with Et3N (1.0 g, 10 mmol) followed by EDC (1.15 g, 6.0 mmol). After stirring for 16 h the solvent was removed, the residue was taken up in H2O (100 mL), and extracted with 3×75 ml portions of EtOAc. The organic extract was washed consecutively with 10% KHSO4, brine, satd. NaHCO3, brine, and dried (Na2SO4). Solvent removal gave a residue that was purified by flash chromatography (silica, 95% hexanes/EtOAc) to give crude 16-4. This was further purified by chromatography (silica, 70%/acetone/hexanes) to give pure 16-4.

Workup

  1. customwas removed
  2. extractionextracted with 3×75 ml portions of EtOAc
  3. extractionThe organic extract
  4. washwas washed consecutively with 10% KHSO4, brine
  5. dry with materialNaHCO3, brine, and dried (Na2SO4)
  6. customSolvent removal
  7. customgave a residue that
  8. customwas purified by flash chromatography (silica, 95% hexanes/EtOAc)
  9. customto give crude 16-4
  10. customThis was further purified by chromatography (silica, 70%/acetone/hexanes)
  11. customto give pure 16-4

Sources & evidence

ORD record
ord-7399d646c9cb4e13a7671e0b36ef12ce
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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