Sodium Hydroxide → [Ethoxycarbonyl-(2-thiophen-2-yl-ethyl)-amino]-acetic acid

HRID 1518545Notes

Reaction equation

HRID 1518545 reaction equation
C([O:3][C:4]([CH2:6][N:7]([CH2:13][CH2:14][C:15]1[S:16][C:17](Br)=[CH:18][CH:19]=1)[C:8](=[O:12])[O:9][CH2:10][CH3:11])=[O:5])C.[OH-].[Na+]>C(O)C>[CH2:10]([O:9][C:8]([N:7]([CH2:6][C:4]([OH:5])=[O:3])[CH2:13][CH2:14][C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59003094Ethyl(ethoxycarbonyl)methyl-2-(5-bromothiophen-2-yl)ethylcarbamate

Product 1

HCID 59302576[Ethoxycarbonyl-(2-thiophen-2-yl-ethyl)-amino]-acetic acidYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To solution of ethyl (ethoxycarbonyl)methyl-2-(5-bromothiophen-2-yl)ethylcarbamate (30.0 g, 105.26 mmol) in ethanol at 0° C. was added dropwise 200 mL of 1N NaOH. The reaction mixture was warmed to RT and stirred for 24 hours. The reaction mixture was extracted with Et2O to remove unreacted starting material and the aqueous layer acidified to pH=1 with 1N HCl. The aqueous solution was extracted with ethyl acetate (2×500 mL) and the combined organics were washed with brine solution, dried (Na2SO4), filtered, and evaporated to obtain crude product. 2-(N-(Ethoxycarbonyl)-N-(2-(thiophen-2-yl)ethyl)amino)acetic acid (74% yield)was obtained as a colorless solid after washing the crude product with pentane; ES-MS: 258.2 (M+H).

Workup

  1. extractionThe reaction mixture was extracted with Et2O
  2. customto remove unreacted
  3. extractionThe aqueous solution was extracted with ethyl acetate (2×500 mL)
  4. washthe combined organics were washed with brine solution
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto obtain crude product

Sources & evidence

ORD record
ord-4df2390de75243c788bb3d7a32674d52
Source dataset
uspto-grants-2012_07
Patent number
US08232406B2

Reaction notes

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