Sodium Iodide → HCID 13922769, compound

HRID 979021Notes

Reaction equation

HRID 979021 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH:13]([CH3:16])[CH:14]=[CH2:15])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C=O)C.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)(O)[O-].[Na+].[I-].[Na+]>C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]([CH:13]([CH3:16])[CH:14]=[CH2:15])[C:10]([O:12][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 12839939HCID 12839939, compound

Product 1

HCID 13922769HCID 13922769, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4.4 mmol of 2-(t-butyloxycarbonylamino)-3-methylpent-4-eneoic acid (2R,3S; 3S,2R) prepared by the method of P. A. Bartlett et al., J. Org. Chem., 1982, 47, 3933, in 10 ml. of dry DMF containing 4.4 mmol of benzyl bromide, 4.4 mmol of sodium bicarbonate and 10 mg. of sodium iodide was stirred for 15 minutes at 20° C. The mixture was dissolved in ethyl acetate, the solution washed three times with water, was dried over sodium sulfate, filtered and evaporated. The ester product was purified by flash chromatography on silica gel. The ester was obtained in an 80% yield as an oil.

Workup

  1. customprepared by the method of P
  2. washthe solution washed three times with water
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe ester product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-9011d7cb2bc24519a3f6c2bbaad32ad2
Source dataset
uspto-grants-1987_05
Patent number
US04666835

Reaction notes

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