Benzoic Acid → L-Tyrosine, N-benzoyl-, ethyl ester

HRID 2229495Notes

Reaction equation

HRID 2229495 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[NH2:6])[CH3:2].[C:16](O)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN1CCOCC1.O.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:15])[C@@H:5]([NH:6][C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1)[CH3:2]

Participants

7

Reactant 5

HCID 243Benzoic AcidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70364L-Tyrosine ethyl esterHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 77033L-Tyrosine, N-benzoyl-, ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

L-Tyrosine ethyl ester (0.28 g, 1.35 mmol) was dissolved in DMF (9 mL). Benzoic acid (1 eq, 1.35 mmol, 0.17 g) was added, followed by N-methylmorpholine (3 eq, 4.06 mmol, 0.45 mL), 1-hydroxybenzotriazole hydrate (1.2 eq, 1.62 mmol, 0.22 g), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (1.2 eq, 1.62 mmol, 0.31 g). The yellow solution was allowed to stir at room temperature under nitrogen for three days. The DMF was then removed by rotary evaporation and the resulting residue partitioned between ethyl acetate and water. The organic portion was separated and washed 3×H2O and 1×aq. saturated NaHCO3. It was dried over MgSO4, filtered, and concentrated to an oil. Trituration with diethyl ether induced formation of a white powder (0.32 g, 76%). MS (ES+) m/e 314 [M+H]+, 627.

Workup

  1. customThe DMF was then removed by rotary evaporation
  2. customthe resulting residue partitioned between ethyl acetate and water
  3. customThe organic portion was separated
  4. washwashed 3×H2O and 1×aq
  5. dry with materialIt was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-82f2a0a79c324a7893b05937fa07bf75
Source dataset
uspto-grants-2002_07
Patent number
US06420424B1

Reaction notes

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