Sodium Iodide → HCID 59737508, compound

HRID 1907702Notes

Reaction equation

HRID 1907702 reaction equation
Cl[CH2:2][C:3]1[CH:30]=[CH:29][C:6]([C:7]([NH:9][C:10]2[CH:15]=[C:14]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[CH:13]=[CH:12][C:11]=2[NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:8])=[CH:5][CH:4]=1.[CH3:31][O:32][CH2:33][C@@H:34]1[CH2:38][CH2:37][CH2:36][NH:35]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(Cl)Cl.CC(C)=O>[CH3:31][O:32][CH2:33][C@@H:34]1[CH2:38][CH2:37][CH2:36][N:35]1[CH2:2][C:3]1[CH:30]=[CH:29][C:6]([C:7]([NH:9][C:10]2[CH:15]=[C:14]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[CH:13]=[CH:12][C:11]=2[NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:8])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 671217(S)-(+)-2-(Methoxymethyl)pyrrolidineHCID 59737342HCID 59737342, compound

Product 1

HCID 59737508HCID 59737508, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of chloride 74 (0.30 g, 0.68 mmol) in DCM (7 mL) was added (S)-2-(methoxymethyl)pyrrolidine (86 mg, 0.75 mmol), K2CO3 (0.31 g, 2.24 mmol) and NaI (12 mg, 0.075 mmol). Acetone (3 mL) was added and the reaction mixture was heated to reflux for 3 days then concentrated. The residue was taken up in AcOEt, washed with H2O, brine, dried over MgSO4, filtered and concentrated to give title compound 75 (0.323 g, 91% yield).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 3 days
  3. concentrationthen concentrated
  4. washwashed with H2O, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-92359e102376425c8dfa09d63df6f225
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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