1,2-Dichloroethane → HCID 66653245, compound

HRID 1524308Notes

Reaction equation

HRID 1524308 reaction equation
[C:1]([CH2:4][C@H:5]([C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([OH:24])=[O:23])[NH:6][C:7](=[O:18])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)(O)=[O:2].C1C=CC2N(O)N=[N:34][C:32]=2C=1.C(Cl)CCl.CCN(CC)CC.CN.C1COCC1>CN(C=O)C.O>[CH3:17][O:16][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][C:11]=1[O:14][CH3:15])[C:7]([NH:6][C@@H:5]([C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([OH:24])=[O:23])[CH2:4][C:1](=[O:2])[NH:34][CH3:32])=[O:18]

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 66653252HCID 66653252, compound

Product 1

HCID 66653245HCID 66653245, compoundYield 158.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[(R)-2-carboxy-1-(3,4-dimethoxy-benzoylamino)-ethyl]benzoic acid (100 mg, 0.268 mmol), HOBt (42 mg, 0.295 mmol), and EDC (58 mg, 0.295 mmol) in DMF (2 mL) add Et3N (0.149 mL, 1.072 mmol). Stir this at room temperature for 2 h, then add 2 M methylamine in THF solution (1.34 mL, 2.68 mmol) and stir the solution at room temperature for 24 h. Dilute the reaction with water (1 mL) and quench with conc. HCl (a few drops). Extract with EtOAc (3×50 mL), wash the organics with water (50 mL) and brine (50 mL) and dry (Na2SO4) and concentrate to a residue in vacuo then dry under P2O5. Triturate the solid in MeOH/EtOAc and filter off the inorganic salts. Concentrate the filtrate and dry in vacuo to a residue. Triturate this in EtOAc/hexane to give 164 mg of 3-[(R)-1-(3,4-dimethoxy-benzoylamino)-2-methylcarbamoyl-ethyl]-benzoic acid as a hydroscopic solid.

Workup

  1. stirringstir the solution at room temperature for 24 h
  2. additionDilute
  3. customquench with conc. HCl (a few drops)
  4. extractionExtract with EtOAc (3×50 mL)
  5. washwash the organics with water (50 mL) and brine (50 mL)
  6. dry with materialdry (Na2SO4)
  7. concentrationconcentrate to a residue in vacuo
  8. customthen dry under P2O5
  9. customTriturate the solid in MeOH/EtOAc
  10. filtrationfilter off the inorganic salts
  11. concentrationConcentrate the filtrate
  12. customdry in vacuo to a residue
  13. customTriturate this in EtOAc/hexane

Sources & evidence

ORD record
ord-18edbbb5cb854901a6f3c3c06f3ecd87
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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