HCID 86588600, compound → HCID 86588601, compound

HRID 2416346Notes

Reaction equation

HRID 2416346 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C@:4]([CH3:21])([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]>C(O)C.CCOC(C)=O.CCCCCC>[CH3:1][O:2][C:3](=[O:22])[C@:4]([CH3:21])([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:13][CH2:4][CH2:3][OH:2])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

Participants

4

Reactant 1

HCID 86588600HCID 86588600, compound

Product 1

HCID 86588601HCID 86588601, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The N-t-butyloxycarbonyl-α-methyltyrosine methylester (1.70 g) from the previous synthesis was dissolved in 25 ml of absolute ethanol and treated with dry sodiun ethoxide (742 mg). 3-Bromopropanol (924 mg, 0.6 ml) was added and the solution was refluxed for 5 hours. The ethanol was then evaporated, 100 ml of dichloromethane added and the solution washed with 100 ml of water. After drying over MgSO4 the solvent was evaporated to yield two spots on a TLC plate developed in EtOAc:Hexane 1:1. The first spot was product and the second was starting material. The product was purified on a silica gel column using EtOAc:Hexane (1:1) A yield of 620 mg (MW 367.2, 31%) was obtained.

Workup

  1. additiontreated
  2. dry with materialwith dry sodiun ethoxide (742 mg)
  3. addition3-Bromopropanol (924 mg, 0.6 ml) was added
  4. temperaturethe solution was refluxed for 5 hours
  5. customThe ethanol was then evaporated
  6. addition100 ml of dichloromethane added
  7. washthe solution washed with 100 ml of water
  8. dry with materialAfter drying over MgSO4 the solvent
  9. customwas evaporated
  10. customto yield two spots on a TLC plate
  11. customThe product was purified on a silica gel column
  12. customwas obtained

Sources & evidence

ORD record
ord-0db1e37966994f1d89819e901e548e72
Source dataset
uspto-grants-2004_11
Patent number
US06824760B2

Reaction notes

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