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

HRID 874081

반응식

HRID 874081 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7b8561a1c8dd467aa7304fb2998c6784
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980326B2

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