Sodium Iodide → Iodomethyl-4[N-(4-nitrobenzyloxycarbonyl)glycylamino]benzoate

HRID 1194929Notes

Reaction equation

HRID 1194929 reaction equation
Cl[CH2:2][O:3][C:4](=[O:29])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:28])[CH2:13][NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])=[CH:7][CH:6]=1.[I-:30].[Na+]>CC(C)=O>[I:30][CH2:2][O:3][C:4](=[O:29])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:28])[CH2:13][NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 21248818HCID 21248818, compound

Product 1

HCID 21248973Iodomethyl-4[N-(4-nitrobenzyloxycarbonyl)glycylamino]benzoateYield 49.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of chloromethyl-4[N-(4-nitrobenzyloxycarbonyl)glycylamino]benzoate (1.0 g) in dry acetone (30 ml) was treated with finely-ground sodium iodide (3.6 g) and the mixture stirred at room temperature for 16 h. The mixture was filtered, the filtrate evaporated under reduced pressure and the residue dissolved in dichloromethane (50 ml) and washed with sodium thiosulphate (10%. aq. solution) until colourless. The organic phase was washed with water (20 ml), saturated aqueous NaCl (20 ml) and dried (MgSO4). The solvent was evaporated and the residue crystallised from ethyl acetate to afford the title compound as a white solid (0.600 g), m.p. 162°-4° C.; νmax (Nujol) 3300, 1735, 1690, 1610, and 1525 cm-1 ; δH (CDCl3 /D6 -DMSO) 3.90 (2H, d, J 6 Hz), 5.23 (2H, s), 6.18 (2H, s), 6.18 (2H, s), and 7.35-8.20 (10H, m).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated under reduced pressure
  3. dissolutionthe residue dissolved in dichloromethane (50 ml)
  4. washwashed with sodium thiosulphate (10%. aq. solution) until colourless
  5. washThe organic phase was washed with water (20 ml), saturated aqueous NaCl (20 ml)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated
  8. customthe residue crystallised from ethyl acetate

Sources & evidence

ORD record
ord-221158e44a0c43589a5dea041c20bed5
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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