Dimethyl Sulfate → HCID 11325332, compound

HRID 1735133Notes

Reaction equation

HRID 1735133 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C@H:5]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[NH:6][C:7]([C:9]1[S:10][C:11]([NH2:14])=[CH:12][CH:13]=1)=[O:8])[CH3:2].[CH3:23]CN(C(C)C)C(C)C.COS(OC)(=O)=O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:22])[C@H:5]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[NH:6][C:7]([C:9]1[S:10][C:11]([NH:14][CH3:23])=[CH:12][CH:13]=1)=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 81531DiisopropylethylamineHCID 10087888HCID 10087888, compound

Product 1

HCID 11325332HCID 11325332, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution containing N-(5-aminothiophene-2-carbonyl)-L-glutamic acid diethyl ester (III-3 where R2 is H) (1.78 g, 5.42 mmol), (i-Pr)2NEt (1.0 mL, 0.74 g, 5.7 mmol), and Me2SO4 (0.59 mL, 0.79 g, 6.2 mmol) in 20 mL N,N-dimethylformamide (DMF) was warmed at 60° C. for 2 hours, then left at 20°-25° C. for 42 hours. The solution was evaporated in vacuo (1 mm, bath 25°-30° C.), and the residue was dissolved in EtOAc-cyclohexane (1:1 by volume) for application to a silica gel column. Elution by the same solvent system afforded fractions homogeneous by TLC of the product. Fractions were combined and evaporated to afford 16% yield (287 mg) of N-[5-(methylamino)thiophene-2-carbonyl]-L-glutamic acid diethyl ester (III-3) R2 =CH3 as an amber oil.

Workup

  1. customThe solution was evaporated in vacuo (1 mm, bath 25°-30° C.)
  2. dissolutionthe residue was dissolved in EtOAc-cyclohexane (1:1 by volume) for application to a silica gel column
  3. washElution by the same solvent system
  4. customafforded fractions homogeneous by TLC of the product
  5. customevaporated

Sources & evidence

ORD record
ord-08a592a2ecee4c80b08f8a821d0bf270
Source dataset
uspto-grants-1996_07
Patent number
US05536724

Reaction notes

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