Phosgene → L-Glutamic acid, 5-(phenylmethyl) ester

HRID 874081

Reaction equation

HRID 874081 reaction equation
O[NH:2][C@H:3]([C:16](N)=[O:17])[CH2:4][CH2:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(Cl)(Cl)=[O:20]>C1COCC1>[NH2:2][C@H:3]([C:16]([OH:17])=[O:20])[CH2:4][CH2:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 131732571HO-Glu(Bzl)-NH2

Product 1

HCID 122337L-Glutamic acid, 5-(phenylmethyl) esterYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

HO-Glu(Bzl)-NH2 (30.0 g, 126.0 mmol) was suspended in 300 mL of anhydrous THF and heated to 50° C. Phosgene (20% in toluene) (81.3 mL, 164.6 mmol) was added to the amino acid suspension by syringe, and the amino acid dissolved over the course of approx. 30 minutes, forming a clear solution. The solution was concentrated by rotory evaporation, dissolved in ˜150 mL of anhydrous THF, and transferred to an Erlenmeyer flask. Hexane was added and the product was allowed to crystallize overnight. The NCA was isolated by filtration and dried in vacuo. 29.8 g (90% yield) of Glu(Bzl) NCA was isolated as a white, crystalline solid. 1H NMR (CDCl3) δ 7.36 (5H), 6.22 (1H), 5.14 (2H), 4.35 (1H), 2.61 (2H), 2.29 (1H), 2.14 (1H) ppm.

Workup

  1. customforming a clear solution
  2. concentrationThe solution was concentrated by rotory evaporation
  3. dissolutiondissolved in ˜150 mL of anhydrous THF
  4. additionHexane was added
  5. customto crystallize overnight
  6. customThe NCA was isolated by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-7b8561a1c8dd467aa7304fb2998c6784
Source dataset
uspto-grants-2015_03
Patent number
US08980326B2

Linked notes

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