Magnesium → HCID 59485687, compound

HRID 1972228Notes

Reaction equation

HRID 1972228 reaction equation
[Cl:1][C:2]1[CH:41]=[CH:40][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C@H:16]([C:24]([O:26][CH2:27]C)=[O:25])[N:15](S(C4C=CC(C)=CC=4)(=O)=O)[C:14]3=[O:39])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[Mg]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C@H:16]([C:24]([O:26][CH3:27])=[O:25])[NH:15][C:14]3=[O:39])=[CH:11][CH:12]=2)=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 5462224MagnesiumHCID 59485673HCID 59485673, compound

Product 1

HCID 59485687HCID 59485687, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (4R,5S)-ethyl 1-(4-(4-chlorophenoxy)phenyl)-2-oxo-5-phenyl-3-tosylimidazolidine-4-carboxylate (15.0 mg, 0.025 mmol) in MeOH (0.5 mL) is added magnesium powder (6.2 mg, 0.25 mmol). The reaction mixture is heated in a sealed tube at 80° C. for 1 h. After cooling down to room temperature, the mixture is quenched with saturated NH4Cl aqueous solution (5 mL) and extracted with EtOAc (3×3 mL). The combined organic layer is concentrated and purified by preparatory TLC to provide the title compound; 1H NMR (CDCl3, 400 MHz) δ 7.39-7.32 (m, 7H), 7.23 (d, 2H), 6.86 (m, 4H), 5.43 (d, 1H), 5.26 (br, 1H), 4.08 (d, 1H), 3.87 (s, 3H); HPLC-MS calculated for C23H19ClN2O4 (M+H+) 423.1, found 423.1.

Workup

  1. temperatureAfter cooling down to room temperature
  2. customthe mixture is quenched with saturated NH4Cl aqueous solution (5 mL)
  3. extractionextracted with EtOAc (3×3 mL)
  4. concentrationThe combined organic layer is concentrated
  5. custompurified by preparatory TLC

Sources & evidence

ORD record
ord-8ee988c77ad448fbad5adce1dbaf5406
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

Loading…