L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl- → HCID 67028705, compound

HRID 1023010Notes

Reaction equation

HRID 1023010 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Rh]>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]1[CH2:15][CH2:16][CH:17]([OH:20])[CH2:18][CH2:19]1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-HCID 178418361HCID 178418361, compound

Product 1

HCID 67028705HCID 67028705, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

0.74 g (7.17 mmol) of rhodium was added to a solution of 7.00 g (24.88 mmol) of (S)-2-tert-butoxycarbonylamino-3-(4-hydroxyphenyl)propionic acid in 50 ml of methanol, and hydrogenation was carried out at 50 C/6 bar pressure of hydrogen. After conversion was complete, the catalyst was filtered off and the filtrate was concentrated. The product was pure enough for further reactions.

Workup

  1. filtrationthe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9e0e387b0c214f0eb5cdc6ed1c227d93
Source dataset
uspto-grants-2014_05
Patent number
US08722655B2

Reaction notes

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