Reaktion #969553

Reaktionsgleichung

Benzyl 2-aminoacetate

benzyl 2-aminoacetate hydrochloride

benzyl 2-aminoacetate

pyridine

1-chloroethyl chloroformate

sodium bicarbonate

→

benzyl 2-((1-chloroethoxy)carbonylamino)acetate

Lösungsmittel

methylene chloride

water

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwash
2. 2
   Sonstigegiving a white precipitate
3. 3
   SonstigeThis cold reaction mixture
4. 4
   Filtrationwas filtered
5. 5
   Sonstigeto remove the solid
6. 6
   Einengenthe filtrate was concentrated to dryness

Vorschrift

Benzyl 2-aminoacetate was generated from a treatment of benzyl 2-aminoacetate hydrochloride (Aldrich) in methylene chloride with aqueous sodium bicarbonate solution followed by water wash. To a cooled solution of benzyl 2-aminoacetate (1.837 g, 11.1 mmol) and pyridine (1.1 g, 1.1 mL, 13.9 mmol) in methylene chloride (17 mL) at −78° C., was added slowly 1-chloroethyl chloroformate (Aldrich, 1.67 g, 11.7 mmol) over ˜10 min. The reaction mixture was allowed to stir at −78° C. for 3 h, giving a white precipitate. This cold reaction mixture was filtered to remove the solid and the filtrate was concentrated to dryness, giving the crude benzyl 2-((1-chloroethoxy)carbonylamino)acetate which was used for the next step without further purification.

Quelle