Triethylamine → HCID 54569424, compound

HRID 375110Notes

Reaction equation

HRID 375110 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][NH:6]1.C([N:13](CC)CC)C.[CH2:18]([O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[CH3:2][O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[NH:13][C:30](=[O:31])[C:29]1[CH:33]=[CH:34][C:26]([O:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 738804-(Benzyloxy)benzoic acidHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 54569424HCID 54569424, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

L-Proline methyl ester hydrochloride (7.2 g, 43.8 mmol) was dissolved in 100 mL of anhydrous DMF at 0° C. To this solution was added triethylamine (4.2 g, 43.8 mmol). After vigorous stirring for 1 hour, the solid triethylamine hydrochloride was removed by filtration. To the filtrate was added 4-benzyloxybenzoic acid (10.0 g, 43.8 mmol) followed by DCC (9.9 g, 48.2 mmol). The reaction mixture was allowed to stir overnight at room temperature. The solid DCU was then removed by filtration, and the filtrated distributed between H2O/ethyl acetate (300 mL ea.). The organic was washed several times with 200 mL portions of H2O to remove DMF. The organic was dried (Na2SO4), and concentrated in vacuo to a solid residue that was chromatographed (SiO2, 15-100% ethyl acetate/hexanes). Isolation provided 5.3 g (35%) of N-(4-benzyloxybenzamido)-L-proline methyl ester as a white solid. MS.

Workup

  1. customthe solid triethylamine hydrochloride was removed by filtration
  2. stirringto stir overnight at room temperature
  3. customThe solid DCU was then removed by filtration
  4. washThe organic was washed several times with 200 mL portions of H2O
  5. customto remove DMF
  6. dry with materialThe organic was dried (Na2SO4)
  7. concentrationconcentrated in vacuo to a solid residue that
  8. customwas chromatographed (SiO2, 15-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ef28dbe5b71f4e02bf936c8cd04bc1c8
Source dataset
uspto-grants-1996_01
Patent number
US05484780

Reaction notes

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