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

HRID 2088334Notes

Reaction equation

HRID 2088334 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 chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of alcohol (5) (0.29 g, 1 mmol) in dichloromethane (10 ml) was treated with thionyl chloride (1 g) and stirred at room temperature under nitrogen overnight. The solvent was removed on a rotary evaporator (bath temperature below 28° C.). Dichloromethane (10 ml) was added and stripped under the same conditions twice. The solid residue was taken in water (8 ml) and washed with MTBE (2×15 ml). The resulting aqueous solution contains pure (6) (LCMS) and was used as such in the next step.

Workup

  1. customThe solvent was removed on a rotary evaporator (bath temperature below 28° C.)
  2. additionDichloromethane (10 ml) was added
  3. washwashed with MTBE (2×15 ml)

Sources & evidence

ORD record
ord-92f51b379efb49bb900d82787f209366
Source dataset
uspto-grants-2013_05
Patent number
US08435956B2

Reaction notes

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