Butyl iodide → HCID 54253050, compound

HRID 1288656Notes

Reaction equation

HRID 1288656 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C@H:5]([CH3:15])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1)[CH3:2].[CH2:17](I)[CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:16])[C@H:5]([CH3:15])[N:6]([C:7]1[CH:8]=[CH:9][C:10]([S:13][CH3:14])=[CH:11][CH:12]=1)[CH2:17][CH2:18][CH2:19][CH3:20])[CH3:2]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 53903419HCID 53903419, compound

Product 1

HCID 54253050HCID 54253050, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(4-Methylthiophenyl)alanine ethyl ester (10.0 g, 42.0 mmol), n-butyl iodide (7.9 g, 42 mmol) and potassium carbonate were added to 150 mL of acetonitrile and the mixture was heated at reflux for 48 h under a nitrogen atmosphere. The reaction mixture was cooled and then partitioned between 300 mL ethyl acetate and 200 mL brine. The organic layer was separated, washed with 100 mL brine, dried over anhyd. sodium sulfate, and concentrated at reduced pressure. The resulting oil was charged onto a silica gel column and eluted with heptane:THF (5:1). The desired ester was isolated as a yellow oil (3.0 g, 24%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 48 h under a nitrogen atmosphere
  3. temperatureThe reaction mixture was cooled
  4. custompartitioned between 300 mL ethyl acetate and 200 mL brine
  5. customThe organic layer was separated
  6. washwashed with 100 mL brine
  7. customdried over anhyd
  8. concentrationsodium sulfate, and concentrated at reduced pressure
  9. additionThe resulting oil was charged onto a silica gel column
  10. washeluted with heptane:THF (5:1)

Sources & evidence

ORD record
ord-ef903a1a30a14706bbb8e2bcdf2b2001
Source dataset
uspto-grants-1998_05
Patent number
US05747235

Reaction notes

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