1,2-Dichloroethane → HCID 131721118, compound

HRID 362698Notes

Reaction equation

HRID 362698 reaction equation
[C:1]([O:5][C:6]([CH:8]([C@@H:19]1[CH2:23][CH2:22][CH2:21][NH:20]1)[N:9]1[CH2:16][CH2:15][C@H:14]([CH2:17][CH3:18])[C@H:10]1[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[Cl:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][CH:46]=1)[CH2:42][NH2:43].CN1CCOCC1>CN(C=O)C>[Cl:38][C:39]1[CH:40]=[C:41]([CH2:42][NH:43][C:11](=[O:13])[C@@H:10]2[C@@H:14]([CH2:17][CH3:18])[CH2:15][CH2:16][N:9]2[CH:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[C@@H:19]2[CH2:23][CH2:22][CH2:21][NH:20]2)[CH:44]=[CH:45][CH:46]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 77802Benzenemethanamine, 3-chloro-HCID 70196590HCID 70196590, compound

Product 1

HCID 131721118HCID 131721118, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[(t-Butyloxycarbonyl)-pyrrolidin-2(S)-ylmethyl]-3(S)-ethyl-proline (0.50 g, 1.53 mmol), EDC (0.293 g, 1.53 mmol), HOBT (0.243 g, 1.53 mmol) and 3-chlorobenzylamine(0.187 mL, 1.53 mmol) were dissolved in DMF (5 mL), the pH adjusted to 7 with N-methyl-morpholine (0.51 mL, 4.6 mmol), and the reaction mixture stirred for 18 hours at ambient temperature. After removing the solvent in vacuo the residue was partitioned between EtOAc and 5% aqueous NaHCO3. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated to give the title compound after chromatography (SiO2, EtOAc:hexane, 2:3).

Workup

  1. customAfter removing the solvent in vacuo the residue
  2. customwas partitioned between EtOAc and 5% aqueous NaHCO3
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f785ed8180da49529e64ed0fb3bbbc87
Source dataset
uspto-grants-1999_02
Patent number
US05869682

Reaction notes

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