Hydrochloric Acid → [Ethoxycarbonyl-(2-thiophen-2-yl-ethyl)-amino]-acetic acid

HRID 1019595Notes

Reaction equation

HRID 1019595 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][N:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:7][CH2:8][C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)C.[OH-].[Na+].Cl>CCO.CCOC(C)=O>[CH2:17]([O:16][C:14]([N:6]([CH2:5][C:4]([OH:19])=[O:3])[CH2:7][CH2:8][C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)=[O:15])[CH3:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66934051[Ethoxycarbonyl-(2-thiophen-2-yl-ethyl)-amino]acetic acid ethyl ester

Product 1

HCID 59302576[Ethoxycarbonyl-(2-thiophen-2-yl-ethyl)-amino]-acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The crude material from step (a) (165 mmol, ˜47 g) was dissolved in EtOH (700 mL) and treated with 600 mL of 1M NaOH. After stirring overnight, the reaction was acidified with concentrated HCl to pH˜1. The crude reaction was diluted with EtOAc (400 mL) and washed with water. The water was back-extracted with EtOAc. The combined organic extracts were washed with water (2×) and dried over MgSO4. Concentration and evaporation from toluene (2×) gave the sub-title product as a solid.

Workup

  1. customThe crude reaction
  2. washwashed with water
  3. extractionThe water was back-extracted with EtOAc
  4. washThe combined organic extracts were washed with water (2×)
  5. dry with materialdried over MgSO4
  6. concentrationConcentration and evaporation from toluene (2×)

Sources & evidence

ORD record
ord-2197c22359c548609cc40eff5fd7c6ff
Source dataset
uspto-grants-2014_05
Patent number
US08716276B2

Reaction notes

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