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

HRID 626643Notes

Reaction equation

HRID 626643 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-d3deae655747429fae1f28bfc6b4c91c
Source dataset
uspto-grants-2016_04
Patent number
US09309207B2

Reaction notes

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