Thionyl Chloride → 3-(2-Chloro-1-ethoxycarbonyl-ethylcarbamoyl)-1-ethoxycarbonyl-propyl-ammonium chloride

HRID 2088335Notes

Reaction equation

HRID 2088335 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([NH2:19])[CH2:6][CH2:7][C:8](=[O:18])[NH:9][CH:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11]O)[CH3:2].S(Cl)([Cl:23])=O>ClCCl>[Cl-:23].[Cl:23][CH2:11][CH:10]([NH:9][C:8]([CH2:7][CH2:6][CH:5]([NH3+:19])[C:4]([O:3][CH2:1][CH3:2])=[O:20])=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 725709632-Amino-4-(1-ethoxycarbonyl-2-hydroxy-ethylcarbamoyl)-butyric acid ethyl ester

Product 1

HCID 866236773-(2-Chloro-1-ethoxycarbonyl-ethylcarbamoyl)-1-ethoxycarbonyl-propyl-ammonium chlorideYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of alcohol 5 (10 g, 35 mmol) in dichloromethane (350 ml) was treated with thionyl chloride (20 mL) and stirred at room temperature under nitrogen overnight. The solvent was removed on a rotary evaporator (bath temperature below 28° C.). Dichloromethane (100 ml) was added and stripped under the same conditions twice. The solid residue was triturated with DCM (100 mL), Heptane (100 mL), and MTBE (100 ml) to give 10 g (84% yield) of pure 6 (LCMS) as a off-white solid.

Workup

  1. customThe solvent was removed on a rotary evaporator (bath temperature below 28° C.)
  2. additionDichloromethane (100 ml) was added
  3. customThe solid residue was triturated with DCM (100 mL), Heptane (100 mL), and MTBE (100 ml)
  4. customto give 10 g (84% yield) of pure 6 (LCMS) as a off-white solid

Sources & evidence

ORD record
ord-f7e788e5d2674ba3900d40327732133a
Source dataset
uspto-grants-2013_05
Patent number
US08435956B2

Reaction notes

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