1,2-Dichloroethane → HCID 13932900, compound

HRID 1779964Notes

Reaction equation

HRID 1779964 reaction equation
[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:33][O:34][C:35](=[O:41])[C@@H:36]1[CH2:40][CH2:39][CH2:38][NH:37]1.C(N(CC)CC)C>CN(C=O)C>[CH3:33][O:34][C:35](=[O:41])[C@@H:36]1[CH2:40][CH2:39][CH2:38][N:37]1[C:9](=[O:11])[CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 64798Diphenylpropionic acidHCID 757711-HydroxybenzotriazoleHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 13932900HCID 13932900, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,3 Diphenylpropionic acid (2.00 g, 8.85 mmol) in DMF (20 mL) was added EDC (2.04 g, 10.62 mmol), HOBT (1.44 g, 10.62 mmol) and L-proline methyl ester hydrochloride (1.76 g, 10.62 mmol) with stirring at ambient temperature. Triethylamine (2.96 mL, 21.24 mmol) was added to adjust the pH of the mixture to 8.5. After 24 hrs the DMF was removed under reduced pressure and the residue was partitioned between EtOAc (100 mL)- H2O (50 mL). The aqueous layer was washed with EtOAc (2×50 mL), organics combined, washed with 10% citric acid soln, aq satd NaHCO3 soln, brine and dried (Na2SO4). Filtration and concentration to dryness gave 3.50 g of crude product which was chromatographed (SiO2)eluting with 99 CH2Cl2 :1 MeOH to 98 CH2Cl2 :2 MeOH to give 2.48 g (83%) of N-(3,3-diphenylpropionyl)-L-proline methylester.

Workup

  1. customAfter 24 hrs the DMF was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc (100 mL)- H2O (50 mL)
  3. washThe aqueous layer was washed with EtOAc (2×50 mL)
  4. washwashed with 10% citric acid soln
  5. dry with materialbrine and dried (Na2SO4)
  6. filtrationFiltration and concentration to dryness
  7. customgave 3.50 g of crude product which
  8. customwas chromatographed (SiO2)eluting with 99 CH2Cl2

Sources & evidence

ORD record
ord-6183f5e3232b4ab385ed4bd3a3dfc197
Source dataset
uspto-grants-1997_05
Patent number
US05629324

Reaction notes

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