1,2-Dichloroethane → HCID 68666540, compound

HRID 1716829Notes

Reaction equation

HRID 1716829 reaction equation
[N:1]1([CH2:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[CH3:44][O:45][C:46](=[O:52])[C@H:47]([C@@H:49]([CH3:51])[OH:50])[NH2:48]>CN(C=O)C>[N:1]1([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([NH:48][C@H:47]([C:46]([O:45][CH3:44])=[O:52])[C@@H:49]([CH3:51])[OH:50])=[O:17])=[CH:18][CH:19]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2734893Methyl L-threoninate hydrochlorideHCID 27354444-(1H-benzimidazol-1-ylmethyl)benzoic acid

Product 1

HCID 68666540HCID 68666540, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[(1H-benzoimidazol-1-yl)methyl]benzoic acid (0.37 g, 1.47 mmol) in dry DMF was treated sequentially with EDC (0.34 g, 1.76 mmol) and HOBt (0.25 g, 1.62 mmol), stirred at room temperature for 30 min, treated sequentially with DIPEA (0.62 mL, 3.6 mmol) and a solution of threonine methyl ester hydrochloride (0.27 g, 1.62 mmol), stirred for 3 h and concentrated under reduced pressure. The resultant residue was partitioned between CH2Cl2 and water. The layers were separated and the organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica, CH2Cl2:CH3OH 95:5) to afford the title product in 64% yield, identified by NMR and mass spectral analyses. LCMS (ESI+) 368 (MH+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resultant residue was partitioned between CH2Cl2 and water
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica, CH2Cl2:CH3OH 95:5)

Sources & evidence

ORD record
ord-e8690fa764b645f7867f93aa02e05d6f
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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