Ethyl chloroformate → HCID 67027247, compound

HRID 446726Notes

Reaction equation

HRID 446726 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][NH:7][CH2:8][CH2:9][C:10]([O:12]CC)=[O:11])=[CH:2]1.C(=O)(O)[O-].[Na+].Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22].[OH-].[K+]>C(O)C>[CH2:24]([O:23][C:21]([N:7]([CH2:6][C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)[CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:22])[CH3:25]

Participants

6

Reactant 4

HCID 10928Ethyl chloroformateHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 61962679HCID 61962679, compound

Product 1

HCID 67027247HCID 67027247, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Compound 1046 (3.36 g, 15.75 mmol) in ethanol (100 mL) was added saturated sodium bicarbonate (25 mL) and ethyl chloroformate (1.801 mL, 18.9 mmol). The reaction mixture was stirred at room temperature overnight, at which point 1.0 M aqueous potassium hydroxide (63.0 mL, 63.0 mmol) was added. The mixture was stirred at room temperature overnight, concentrated under reduced pressure, made acidic with 6N HCl, and extracted with 10% nBuOH in chloroform. The organics were concentrated to give 3-(ethoxycarbonyl(thiophen-3-ylmethyl)amino)propanoic acid as a tan oil (Compound 1048, 2.04 g, 50%); 1H NMR (300 MHz, CDCl3): δ 7.56-7.48 (m, 1H), 7.44-7.38 (m, 2H), 4.75 (s, 2H), 4.49-4.39 (m, 4H), 3.92-3.77 (m, 2H), 2.62-2.58 (m, 2H) and 1.68-1.48 (m, 3H).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature overnight
  3. concentrationconcentrated under reduced pressure
  4. extractionextracted with 10% nBuOH in chloroform
  5. concentrationThe organics were concentrated

Sources & evidence

ORD record
ord-94f485a8be9041a49b1fcdd5840f5ba6
Source dataset
uspto-grants-2013_07
Patent number
US08481524B2

Reaction notes

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