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Dimethyl Sulfoxide → N-(tert-Butoxycarbonyl)-4-carbamoyl-2,6-dimethyl-L-phenylalanine

HRID 2371014
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2371014
C[O:2][C:3](=[O:24])[C@@H:4]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]#[N:14])=[CH:8][C:7]=1[CH3:15].CS(C)=[O:27].C([O-])([O-])=O.[K+].[K+].OO>O>[C:20]([O:19][C:17]([NH:16][C@@H:4]([CH2:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13](=[O:27])[NH2:14])=[CH:8][C:7]=1[CH3:15])[C:3]([OH:2])=[O:24])=[O:18])([CH3:23])([CH3:22])[CH3:21]
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Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 46218695(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-cyano-2,6-dimethylphenyl)propanoate

Produkt 1

HCID 11847987N-(tert-Butoxycarbonyl)-4-carbamoyl-2,6-dimethyl-L-phenylalanine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

A 50 mL three-necked round bottom flask equipped with magnetic stirrer, and thermocouple was charged under nitrogen with (S)-2-tert-butoxycarbonylamino-3-(4-cyano-2,6-dimethyl-phenyl)-propionic acid methyl ester (166.2 mg, 0.5 mmol), DMSO (5.0 mL), and K2CO3 (75 mg, 0.5 mmol) and the resulting mixture cooled in an ice bath. To the resulting mixture was then added 30% H2O2 (110 μl), dropwise via a syringe. The resulting mixture was then allowed to warm up to ambient temperature, with the solids observed to dissolve to yield a clear solution. After stirring for about 2 hours at 45-50° C., water (10 mL) was added, cooling was applied, and a precipitated product isolated by filtration. The isolated white solid was washed with water (2×25 mL), then dried for 24 hours on high vacuum pump to yield the title compound as a white solid.

Aufarbeitung

  1. customA 50 mL three-necked round bottom flask equipped with magnetic stirrer
  2. temperaturethe resulting mixture cooled in an ice bath
  3. dissolutionto dissolve
  4. customto yield a clear solution
  5. temperaturecooling
  6. customa precipitated product isolated by filtration
  7. washThe isolated white solid was washed with water (2×25 mL)
  8. customdried for 24 hours on high vacuum pump

Quellen und Nachweise

ORD-Eintrag
ord-ac98cc9a3c204299bfeb198a140e7d6f
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08710256B2

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