Sodium Iodide → HCID 53905191, compound

HRID 1885419Notes

Reaction equation

HRID 1885419 reaction equation
[CH2:1]([O:8][C:9](=[O:27])[C@H:10]([CH2:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[NH:11][C:12](=[O:15])[CH2:13]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:28].[Na+]>CC(=O)CC>[CH2:1]([O:8][C:9](=[O:27])[C@H:10]([CH2:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[NH:11][C:12](=[O:15])[CH2:13][I:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 54439852HCID 54439852, compound

Product 1

HCID 53905191HCID 53905191, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of N-α-chloroacetyl-L-aspartic acid dibenzyl ester (111 g, 0.285 mol) and sodium iodide (59.5 g, 0.40 mol) in 2-butanone was heated at reflux for a period of 1.5 hours. The reaction mixture was concentrated to dryness and the residue was added to a separatory funnel containing ethyl acetate (about 500 mL). The aqueous phase was removed and the organic phase was first extracted with brine (about 250 mL) and then dried over sodium sulfate. The resulting solution was then concentrated in vacuo to provide product 12 (136 g, 0.283 mol, 99%) as a viscous brown oil which slowly crystallized over a period of several days at room temperature. Satisfactory 1H NMR data were obtained for this material. This material was not further purified but was instead used directly in the preparation of 9.

Workup

  1. temperatureat reflux for a period of 1.5 hours
  2. concentrationThe reaction mixture was concentrated to dryness
  3. additionthe residue was added to a separatory funnel
  4. additioncontaining ethyl acetate (about 500 mL)
  5. customThe aqueous phase was removed
  6. extractionthe organic phase was first extracted with brine (about 250 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationThe resulting solution was then concentrated in vacuo

Sources & evidence

ORD record
ord-518143cf9dd443da90fb88ba32f4e755
Source dataset
uspto-grants-1992_09
Patent number
US05144073

Reaction notes

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