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

HRID 2058398Notes

Reaction equation

HRID 2058398 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 mmols) of Z-Tyr(But)-OMe (Ann. Chem. 696, page 226 (1966)) were dissolved in 1 l of methanol and catalytically hydrogenated (Pd/BaSO4 catalyst) at pH 4.5 on the autoburette (addition of about 2 N methanolic HCl). When the hydrogenation was complete, the catalyst was filtered off with suction and the filtrate was concentrated. The residue was triturated with ether.

Workup

  1. filtrationthe catalyst was filtered off with suction
  2. concentrationthe filtrate was concentrated
  3. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-fc7ece1ab4804c53a69a69978249eb9c
Source dataset
uspto-grants-1980_07
Patent number
US04215037

Reaction notes

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