Dimethylformamide → Ethyl 4-(2-(tert-butoxycarbonylamino)ethyl)benzoate

HRID 587925Notes

Reaction equation

HRID 587925 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].I[CH2:32][CH3:33]>O.C([O-])(O)=O.[Na+]>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([O:17][CH2:32][CH3:33])=[O:16])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 166409054-(2-{[(Tert-butoxy)carbonyl]amino}ethyl)benzoic acid

Product 1

HCID 67360059Ethyl 4-(2-(tert-butoxycarbonylamino)ethyl)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 1.96 g (7.39 mmol) of 4-(2-(tert-butoxycarbonylamino)ethyl)benzoic acid in 25 mL, of DMF was added 4.43 g (32.1 mmol) of potassium carbonate and 3.00 mL (37.2 mmol) of iodoethane at 0° C. The mixture was warmed to 22° C. and stirred for about 16 h. The reaction was then diluted with 20 ml, of water and 100 mL of saturated NaHCO3. The mixture was extracted with DCM (3×200 mL) and the combined organics were washed with 100 mL of water, dried (MgSO4) and evaporated to give ethyl 4-(2-(tert-butoxycarbonylamino)ethyl)benzoate as a sticky off-white solid.

Workup

  1. extractionThe mixture was extracted with DCM (3×200 mL)
  2. washthe combined organics were washed with 100 mL of water
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-dd478004984d47f3a590e227e194f9f5
Source dataset
uspto-grants-2016_01
Patent number
US09227918B2

Reaction notes

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