Thionyl Chloride → [Benzyl-(2-chloro-1-methylethyl)-amino]acetic acid tert-butyl ester

HRID 1912426Notes

Reaction equation

[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:9]([CH3:12])[CH2:10]O)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:23])=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:9]([CH3:12])[CH2:10][Cl:23])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of an optically-active compound of [benzyl-(2-hydroxy-1-methylethyl)-amino]acetic acid tert-butyl ester (160.0 g) in chloroform (640 ml) cooled to 0° C. was added dropwise thionyl chloride (50.0 ml), and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was cooled to 0° C. Then, thereto were added saturated aqueous sodium bicarbonate solution (1000 ml) and chloroform (100 ml), and the mixture was stirred. The separated organic layer was washed with saturated aqueous sodium chloride solution (500 ml), and the aqueous layer was extracted with chloroform (450 ml) again. The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the titled compound (172.9 g).

Workup

temperatureThe reaction mixture was cooled to 0° C
stirringthe mixture was stirred
washThe separated organic layer was washed with saturated aqueous sodium chloride solution (500 ml)
extractionthe aqueous layer was extracted with chloroform (450 ml) again
dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-4197bcef3b754de489e2486bb8ec9e1a
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609647B2

Reaction notes

Loading…