Potassium Iodide → HCID 70053829, compound

HRID 345228Notes

Reaction equation

HRID 345228 reaction equation
Br[CH2:2][C:3]([CH2:5]Br)=[O:4].[CH2:7]([O:14][C:15]([NH:17][C@H:18]([C:26]([NH:28][C@H:29]([C:31]([OH:33])=[O:32])[CH3:30])=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[C:36]=1[OH:42].[I-].[K+].C(OCC)(=O)C.CN([CH:54]=[O:55])C>>[CH3:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[C:36]=1[O:42][CH2:2][C:3]([CH2:5][O:55][C:54]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:7])=[O:4].[CH2:7]([O:14][C:15]([NH:17][C@H:18]([C:26]([NH:28][C@H:29]([C:31]([OH:33])=[O:32])[CH3:30])=[O:27])[CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:16])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 113352,6-DimethylphenolHCID 88127025HCID 88127025, compound

Product 1

HCID 70053829HCID 70053829, compoundYield 49%

Procedure

N-Benzyloxycarbonyl-L-phenylalanyl-L-alanine bromomethyl ketone (50 mg, 0.11 mmol) and 2,6-dimethylphenol (14 mg) were dissolved in dry DMF (5 mL) and blanketed with argon gas. The solution was treated with potassium iodide on alumina (80 mg, KF-alumina, 2:3) and stirred overnight at room temperature. Ethyl acetate was added and the inorganic salts were removed by filtration. The organic filtrate was washed with saturated NaCl solution (4×25 mL), then dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was applied to a silica gel column. Then N-benzyloxycarbonyl-L-phenylalanyl-L-alanine 2,6-dimethylphenoxymethyl ketone was eluted with EtOAc/hexane (1:1) under pressure. Evaporation gave a white solid (30 mg, 49%), m.p. 167°-168° C.

Workup

  1. customthe inorganic salts were removed by filtration
  2. washThe organic filtrate was washed with saturated NaCl solution (4×25 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. washThen N-benzyloxycarbonyl-L-phenylalanyl-L-alanine 2,6-dimethylphenoxymethyl ketone was eluted with EtOAc/hexane (1:1) under pressure
  6. customEvaporation

Sources & evidence

ORD record
ord-85437cae12984cd791f67a0a03a8dc49
Source dataset
uspto-grants-1991_10
Patent number
US05055451

Reaction notes

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