Triethylamine → HCID 54569424, compound

HRID 1609756Notes

Reaction equation

HRID 1609756 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-760c92223d4b497a8db9ef40c2b7665e
Source dataset
uspto-grants-1995_03
Patent number
US05401851

Reaction notes

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