Thionyl Chloride → HCID 22851087, compound
Reaction equation
C([O:8][C:9]([NH:11][C@@H:12]([CH2:16][NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C:13]([OH:15])=[O:14])=O)C1C=CC=CC=1.S(Cl)(Cl)=O>C(Cl)Cl>[CH2:21]([O:20][C:18]([NH:17][CH2:16][C@H:12]1[C:13](=[O:15])[O:14][C:9](=[O:8])[NH:11]1)=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Suspend the product of Step A (2 g) in CH2Cl2 (25 mL) and treat with thionyl chloride (1.6 mL). Stir the resulting mixture at room temperature for 1 hr and then heat under reflux for 1.5 hr. Concentrate the mixture in vacuo and triturate with hexane (3 times). Dissolve the residue in CH2Cl2 (10 mL), treat with hexane (30 mL), and stir overnight. Filter to give 4(S)-benzyloxycarbonylaminomethyl-2,5-oxazolidinedione.