Hydrochloric Acid → Methyl O-tert-butyl-L-tyrosinate hydrochloride

HRID 2057845Notes

Reaction equation

HRID 2057845 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:15]([O:17][CH3:18])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=1.[ClH:29]>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[NH2:1][C@H:2]([C:15]([O:17][CH3:18])=[O:16])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]([CH3:14])([CH3:12])[CH3:13])=[CH:8][CH:9]=1.[ClH:29]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 7019804O-(1,1-Dimethylethyl)-N-[(phenylmethoxy)carbonyl]-L-tyrosine methyl ester

Product 1

HCID 6452451Methyl O-tert-butyl-L-tyrosinate hydrochloride

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent

Procedure

300 g (778 mmoles) of Z-Tyr(But)-OMe (Ann. Chem. 696, 226 (1966)) are dissolved in 1 liter of methanol and hydrogenated catalytically (Pd/BaSO4 catalyst) at pH 4.5, using an auto-burette (about 2 N methanolic HCl being added). After completion of hydrogenation, the catalyst is filtered off and the filtrate is concentrated. The residue is triturated with ether.

Workup

  1. filtrationAfter completion of hydrogenation, the catalyst is filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe residue is triturated with ether

Sources & evidence

ORD record
ord-1056f3f79e874fd4a3a7c1eba6adf64f
Source dataset
uspto-grants-1980_07
Patent number
US04212796

Reaction notes

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