Sodium Iodide → HCID 86584786, compound

HRID 1634845Notes

Reaction equation

HRID 1634845 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:32])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([N:21]2[CH2:26][CH2:25][CH:24]([CH:27](OC)[O:28]C)[CH2:23][CH2:22]2)(=[O:20])=[O:19])=[CH:14][CH:13]=1)=[O:4].[I-].[Na+].ClC([SiH3])(Cl)Cl>C(#N)C>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:32])[NH:11][C:12]1[CH:13]=[CH:14][C:15]([S:18]([N:21]2[CH2:26][CH2:25][CH:24]([CH:27]=[O:28])[CH2:23][CH2:22]2)(=[O:20])=[O:19])=[CH:16][CH:17]=1)=[O:4]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 69999538HCID 69999538, compoundHCID 71317501CID 71317501

Product 1

HCID 86584786HCID 86584786, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under anhydrous conditions, a solution of (2s)-1-[4-(4-dimethoxymethyl-piperidine-1-sulfonyl)-phenylcarbamoyl]-pyrrolidine-2-carboxylic acid methyl ester (0.240 g, 0.5 mmol), sodium iodide (0.192 g, 1.28 mmol), and trichloromethylsilane (0.120 mL, 1.1 mmol) in acetonitrile (2.5 mL) was stirred at ambient temperature for 15 minutes. The reaction mixture was quenched with water and partitioned with methylene chloride. The organic phase was washed with Na2S2O3 dilute solution and dried (Na2SO4). Removal of solvent afforded the crude product which was used directly in the next step without characterization.

Workup

  1. customThe reaction mixture was quenched with water
  2. custompartitioned with methylene chloride
  3. washThe organic phase was washed with Na2S2O3 dilute solution
  4. dry with materialdried (Na2SO4)
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-effd3fe7a8a54565a4f0848212fdd55f
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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