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

HRID 534685Notes

Reaction equation

HRID 534685 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 mol), DMSO (5.0 mL), and K2CO3 (75 mg, 0.5 mol) 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-111d746d300f4b54b65e81c82b583a3a
Source dataset
uspto-grants-2014_10
Patent number
US08853445B2

Reaction notes

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