Benzyl chloroformate → 3-(1,1-Dimethylethyl)-N-[(phenylmethoxy)carbonyl]-L-tyrosine methyl ester

HRID 1383714Notes

Reaction equation

HRID 1383714 reaction equation
[NH2:1][C@H:2]([C:15]([O:17][CH3:18])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.C([O-])(O)=O.[Na+].[CH:24]1[CH:29]=[CH:28][C:27]([CH2:30][O:31][C:32](Cl)=[O:33])=[CH:26][CH:25]=1>O.C(OCC)(=O)C>[NH:1]([C:32]([O:31][CH2:30][C:27]1[CH:28]=[CH:29][CH:24]=[CH:25][CH:26]=1)=[O:33])[C@H:2]([C:15]([O:17][CH3:18])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:12])[CH3:13])[CH:5]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 15549498Tyr(3-tBu)-OMe

Product 1

HCID 155494893-(1,1-Dimethylethyl)-N-[(phenylmethoxy)carbonyl]-L-tyrosine methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Tyr(3-tBu)-OMe (1.1 g) in H2O (10 ml), 0.7 g (6.57 mmol) of NaHCO3 and 0.92 ml (6.57 mmol) of Z-Cl were added under cooling with ice and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate and washed with water and saturated brine. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate:n-hexane=1:2) to give Z-Tyr(3-t-Bu)-OMe in the amount of 1.44 g (85%).

Workup

  1. temperatureunder cooling with ice
  2. washwashed with water and saturated brine
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe resulting residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate:n-hexane=1:2)

Sources & evidence

ORD record
ord-d006d3b48f524eaca4b4f1d340b12881
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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