Water → ethyl (S)-2-tert-butoxycarbonylamino-3-(4-but-2-ynyloxy-phenyl)-propionate

HRID 1779218

반응식

HRID 1779218 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:24][C:25]#[C:26][CH3:27].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:24][C:25]#[C:26][CH3:27])=[CH:18][CH:17]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium Carbonate2회HCID 27568621-Bromo-2-butyne2회HCID 11077750Ethyl N-(tert-butoxycarbonyl)-L-tyrosinate

생성물 1

HCID 90060290ethyl (S)-2-tert-butoxycarbonylamino-3-(4-but-2-ynyloxy-phenyl)-propionate수율 89.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

A commercially available reagent of ethyl (S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionate (4.84 g, 15.6 mmol) was dissolved in N,N-dimethylformamide (39 mL), and 1-bromo-2-butyne (1.65 mL, 18.8 mmol) and potassium carbonate (3.25 g, 23.5 mmol) were then added at room temperature. After stirring at 60° C. for 6 hours, and the reaction solution was cooled to room temperature. 1-Bromo-2-butyne (0.55 mL, 6.28 mmol) was added at room temperature, and the mixture was then stirred at 60° C. for 5 hours. The reaction solution was cooled to room temperature, and potassium carbonate (0.433 g, 3.13 mmol) was then added. After stirring at 60° C. for 4.5 hours, the reaction solution was cooled to room temperature. Water (70 mL) was added, and the mixture was then extracted twice with ethyl acetate (70 mL). The organic layer was washed with saturated aqueous solution (30 mL) of sodium chloride, dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure. The residue was purified on Biotage (silica gel, n-hexane/ethyl acetate) to obtain 5.02 g (13.9 mmol, yield 89%) of ethyl (S)-2-tert-butoxycarbonylamino-3-(4-but-2-ynyloxy-phenyl)-propionate.

후처리

  1. temperaturethe reaction solution was cooled to room temperature
  2. stirringthe mixture was then stirred at 60° C. for 5 hours
  3. temperatureThe reaction solution was cooled to room temperature
  4. stirringAfter stirring at 60° C. for 4.5 hours
  5. temperaturethe reaction solution was cooled to room temperature
  6. extractionthe mixture was then extracted twice with ethyl acetate (70 mL)
  7. washThe organic layer was washed with saturated aqueous solution (30 mL) of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. distillationThe solvent was distilled off under reduced pressure
  11. customThe residue was purified on Biotage (silica gel, n-hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-47bbd15c06034dc08fd654ef9f97c86c
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266853B2

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