Potassium Carbonate → HCID 86615225, compound

HRID 2383279Notes

Reaction equation

HRID 2383279 reaction equation
[CH3:1][O:2][C:3](=[O:6])[CH2:4][SH:5].C(=O)([O-])[O-].[K+].[K+].[C:13]([O:17][C:18](=[O:21])[CH2:19]Br)([CH3:16])([CH3:15])[CH3:14]>CN(C)C=O>[C:13]([O:17][C:18](=[O:21])[CH2:19][S:5][CH2:4][C:3]([O:2][CH3:1])=[O:6])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 86615225HCID 86615225, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of mercapto-acetic acid methyl ester (1.0 g, 9.42 mmol) in dimethylformamide (10 mL) at room temperature was added potassium carbonate (1.69 g) followed by bromo-acetic acid tert-butyl ester (1.84 g, 9.42 mmol). The resulting suspension was stirred at ambient temperature overnight and then diluted with hexanes. The organic layer was washed with water three times and brine once, dried over sodium sulfate, filtered and concentrated to give a colorless oil, which was used directly in next step without purification. 1H NMR (CDCl3, 300 MHz) δ (ppm): 3.72 (s, 3H), 3.37 (s, 2H), 3.27 (s, 2H), 1.45 (s, 9H).

Workup

  1. washThe organic layer was washed with water three times and brine once
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a colorless oil, which
  6. customwas used directly in next step without purification

Sources & evidence

ORD record
ord-f740c910472240b8a244b830bf8a8781
Source dataset
uspto-grants-2012_09
Patent number
US08263618B2

Reaction notes

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