Hydrochloric Acid → (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propanoic acid

HRID 1589884Notes

Reaction equation

HRID 1589884 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:21]([OH:23])=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24]OS(OC)(=O)=O.Cl>[OH-].[Na+]>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:21]([OH:23])=[O:22])[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:24])=[CH:18][CH:19]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6497Dimethyl Sulfate2×HCID 712438N-benzyloxycarbonyl-l-tyrosine

Product 1

HCID 10496574(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propanoic acidYield 18%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

N-Benzyloxycarbonyl-L-tyrosine (31.5 g, 0.1 mol) was dissolved in aqueous sodium hydroxide (10 g in 100 ml H2O) and dimethylsulphate (10.5 ml, 0.11 mol) added dropwise to the stirred solution. The reaction was stirred overnight, additional dimethylsulphate (2 ml) added in one portion and the reaction stirred for a further 48 hours. 2M Hydrochloric acid was added until a white precipitate formed. This was filtered off, taken up in ethyl acetate, washed with brine and dried over anhydrous sodium sulphate, filtered and evaporated. The residue was crystallised from ethyl acetate to give N-benzyloxycarbonyl-O-methyl-L-tyrosine (5.8 g, 18%) as a white crystalline solid.

Workup

  1. stirringthe reaction stirred for a further 48 hours
  2. customformed
  3. filtrationThis was filtered off
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-6ade8c84c313481b98263194078b9f1d
Source dataset
uspto-grants-1993_04
Patent number
US05200412

Reaction notes

Loading…