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

HRID 714012Notes

Reaction equation

HRID 714012 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0f3074e6adfa4077a5293b4820825f82
Source dataset
uspto-grants-2015_11
Patent number
US09187408B2

Reaction notes

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