Ethanol → 3-tert-butyl-L-tyrosine

HRID 429931Notes

Reaction equation

HRID 429931 reaction equation
CCO.[O:4]=[C:5]1[C@H:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=2)[NH:9][C@@H](C2C=CC=CC=2)[C@@H](C2C=CC=CC=2)[O:6]1>C1COCC1.Cl[Pd]Cl>[C:19]([C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[OH:18])[CH2:11][C@@H:10]([C:5]([OH:6])=[O:4])[NH2:9])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 2

HCID 702Ethanol2×HCID 57303814(2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-tert-butyl-4-hydroxybenzyl)morpholine

Product 1

HCID 206376913-tert-butyl-L-tyrosineYield 105.9%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a 300 mL Parr bottle were added 0.73 g of PdCl2 and 20 mL of 1:1 THF:EtOH. To this was added a solution of 2.43 g of (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-tert-butyl-4-hydroxybenzyl)morpholine in 80 mL of 1:1 THF:EtOH. The mixture was deoxygenated by bubbling nitrogen through for 10 min and was hydrogenated at 45 psi for 18 h. The vessel was purged with nitrogen, catalyst removed by filtration, and the filtrate concentrated in vacuo. The residue was partitioned between water and hexane. The aqueous solution was washed with four additional 50 mL portions of hexane, subjected to brief rotary evaporation to remove residual hexane, frozen and lyophilized to afford 1.47 g (92%) of 3-tert-butyl-L-tyrosine.HCl as a tan hygroscopic solid.

Workup

  1. customThe mixture was deoxygenated
  2. customby bubbling nitrogen through for 10 min
  3. customThe vessel was purged with nitrogen, catalyst
  4. customremoved by filtration
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe residue was partitioned between water and hexane
  7. washThe aqueous solution was washed with four additional 50 mL portions of hexane
  8. customsubjected to brief rotary evaporation
  9. customto remove residual hexane
  10. temperaturefrozen

Sources & evidence

ORD record
ord-c9859dc7bd374c8fb8342b5540b225ae
Source dataset
uspto-grants-2001_11
Patent number
US06319702B1

Reaction notes

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