L-Tyrosine → tert-Butyl (2S)-2-amino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionate

HRID 1759695Notes

Reaction equation

HRID 1759695 reaction equation
[NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.CN([CH:17]=[O:18])C>>[CH2:11]([O:12][C:17](=[O:18])[CH2:6][CH2:7][CH2:8][O:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][C@@H:2]([C:11]([O:13][C:4]([CH3:9])([CH3:5])[CH3:3])=[O:12])[NH2:1])=[CH:9][CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 6057L-TyrosineHCID 6228Dimethylformamide2×

Product 1

HCID 15512208tert-Butyl (2S)-2-amino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionate

Procedure

Potassium tertbutylate (3.36 g, 30 mmoles) is added to a solution of tyrosine 4-1 (5 g, 21 mmoles) in 100 ml of DMF, followed by agitating for 30 minutes while cooling down in a water+ice bath, then the bromoester (ethyl 4-bromobutanoate) (3.6 ml, 25 mmoles) in solution in 10 ml of DMF is added. The reaction medium is agitated overnight at ambient temperature, followed by evaporating under reduced pressure, taking up the dry extract in a water/ethyl acetate mixture, decanting, drying the organic phase, filtering, evaporating then purifying by chromatography eluting with a Heptane/ethyl acetate gradient (100/0→0/100). 5.2 g of the expected product 4-2 is obtained.

Workup

  1. temperaturewhile cooling down in a water+ice bath
  2. stirringThe reaction medium is agitated overnight at ambient temperature
  3. customby evaporating under reduced pressure
  4. extractionextract in a water/ethyl acetate mixture
  5. customdecanting
  6. customdrying the organic phase
  7. filtrationfiltering
  8. customevaporating
  9. customthen purifying by chromatography
  10. washeluting with a Heptane/ethyl acetate gradient (100/0→0/100)

Sources & evidence

ORD record
ord-59323992f8de4a719a3b261c1101dad0
Source dataset
uspto-grants-2005_01
Patent number
US06838453B2

Reaction notes

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