1,2-Dichloroethane → HCID 54704632, compound

HRID 2214651Notes

Reaction equation

HRID 2214651 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:5][N:6]([CH3:22])[C:7]([C:9]1[CH2:13][N:12]([CH2:14][CH2:15][CH2:16][C:17](O)=[O:18])[C:11](=[O:20])[C:10]=1[OH:21])=[O:8].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:41][NH:42][CH3:43]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:5][N:6]([CH3:22])[C:7]([C:9]1[CH2:13][N:12]([CH2:14][CH2:15][CH2:16][C:17](=[O:18])[N:42]([CH3:43])[CH3:41])[C:11](=[O:20])[C:10]=1[OH:21])=[O:8]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 54691713HCID 54691713, compound2×

Product 1

HCID 54704632HCID 54704632, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{4-[(3,4-dichloro-benzyl)-methyl-carbamoyl]-3-hydroxy-2-oxo-2,5-dihydro-pyrrol-1-yl}-butyric acid, Compound 24, (0.06 g, 0.15 mmol) in dichloromethane (1 mL) was added EDC (0.057 g, 0.3 mmol), HOBT (0.0020 g, 0.015 mmol) and dimethyl amine (0.15 mL, 2 M solution in THF, 0.30 mmol). The mixture was stirred at room temp for 6 h then concentrated and the crude product purified by preparative HPLC (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA) to yield the title compound as an amber oil (0.0147 g, 23% yield). HRMS (M+H) calcd for C19H24N3Cl2O4: 428.11440. found: 428.1143.

Workup

  1. concentrationthen concentrated
  2. customthe crude product purified by preparative HPLC (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA)

Sources & evidence

ORD record
ord-912d817b24c04caab7d5375041500699
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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