Sodium Iodide → HCID 86758802, compound

HRID 1634847Notes

Reaction equation

HRID 1634847 reaction equation
[CH2:1]([O:8][C:9](=[O:42])[C@@H:10]([NH:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:31]2[CH2:36][CH2:35][CH:34]([CH:37](OC)[O:38]C)[CH2:33][CH2:32]2)(=[O:30])=[O:29])=[CH:24][CH:23]=1)=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[Na+].ClC([SiH3])(Cl)Cl>C(#N)C>[CH2:1]([O:8][C:9](=[O:42])[C@@H:10]([NH:18][C:19]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([S:28]([N:31]2[CH2:36][CH2:35][CH:34]([CH:37]=[O:38])[CH2:33][CH2:32]2)(=[O:30])=[O:29])=[CH:26][CH:27]=1)=[O:20])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 69999763HCID 69999763, compoundHCID 71317501CID 71317501

Product 1

HCID 86758802HCID 86758802, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under anhydrous conditions, a solution of (2S)-2-{3-[4-(4-dimethoxymethyl-piperidine-1-sulfonyl)-phenyl]-ureido}-3-phenyl-propionic acid benzyl ester (0.78 g, 1.3 mmol), sodium iodide (0.491 g, 3.27 mmol), and trichloromethylsilane (0.308 mL, 2.62 mmol) in acetonitrile (20 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-b28afa6500ac4999a9fdc03d04ad6f0b
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

Loading…