Water → HCID 9818786, compound

HRID 2229496Notes

Reaction equation

HRID 2229496 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C@H:5]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[NH:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].[C:24]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:23])[C@@H:5]([NH:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:24])=[CH:18][CH:17]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium Carbonate2×HCID 77033L-Tyrosine, N-benzoyl-, ethyl ester

Product 1

HCID 9818786HCID 9818786, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Benzoyl-L-tyrosine ethyl ester (0.054 g, 0.17 mmol) was dissolved in DMF (1 mL). K2CO3 (1 eq, 0.17 mmol, 0.024g) was added, followed by methyl iodide (1 eq, 0.17 mmol, 0.011 mL). The slightly cloudy mixture was allowed to stir at room temperature under nitrogen for 3.5 hours. An additional 2 eq K2CO3 was added and the mixture was allowed to stir overnight. Water was poured into the flask, causing cloudiness. Precipitation was completed via refrigeration. The resulting white solid was filtered, washed well with water and dried in air (0.030 g, 54%).

Workup

  1. stirringto stir overnight
  2. customPrecipitation
  3. filtrationThe resulting white solid was filtered
  4. washwashed well with water
  5. customdried in air (0.030 g, 54%)

Sources & evidence

ORD record
ord-7748fc7aee9c4fd8b5a62da17ee1d493
Source dataset
uspto-grants-2002_07
Patent number
US06420424B1

Reaction notes

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