1-Bromopropane → N-benzyloxycarbonyl-3-[4-propoxyphenyl]-alanine-methyl ester

HRID 1418790Notes

Reaction equation

HRID 1418790 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[H-].[Na+].[CH2:27](Br)[CH2:28][CH3:29].C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH2:27][CH2:28][CH3:29])=[CH:21][CH:22]=1)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

7

Reactant 4

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 7010613N-[(Phenylmethoxy)carbonyl]-L-tyrosine methyl ester

Product 1

HCID 22940772N-benzyloxycarbonyl-3-[4-propoxyphenyl]-alanine-methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4.94 g (15 mmol) of N-benzyloxycarbonyl-tyrosine-methyl ester is dissolved in 25 ml of anhydrous N,N-dimethylformamide and mixed at 5° C. under argon with 0.61 g (15.5 mmol) of sodium hydride dispersion (60% in mineral oil). The batch is allowed to stir for 10 minutes, then 1.91 g (15.5 mmol) of propyl bromide is added, the reaction temperature is allowed to increase to room temperature and it is stirred for another two hours. For working-up, the batch is taken up in ethyl acetate and shaken out several times against aqueous sodium bicarbonate solution. The organic phase is separated, dried on magnesium sulfate, filtered and concentrated by evaporation. The residue is chromatographed for purification on silica gel with hexane/diethyl ether/triethylamine.

Workup

  1. stirringit is stirred for another two hours
  2. customThe organic phase is separated
  3. customdried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed for purification on silica gel with hexane/diethyl ether/triethylamine

Sources & evidence

ORD record
ord-1b1b6d4e4479430986678588eb86f835
Source dataset
uspto-grants-1999_03
Patent number
US05885548

Reaction notes

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