Thionyl Chloride → HCID 22851087, compound

HRID 487864Notes

Reaction equation

HRID 487864 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]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 7019700HCID 7019700, compound

Product 1

HCID 22851087HCID 22851087, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. temperatureheat
  2. temperatureunder reflux for 1.5 hr
  3. concentrationConcentrate the mixture in vacuo
  4. customtriturate with hexane (3 times)
  5. dissolutionDissolve the residue in CH2Cl2 (10 mL)
  6. additiontreat with hexane (30 mL)
  7. stirringstir overnight
  8. filtrationFilter

Sources & evidence

ORD record
ord-12a24e0cab6b40dda7a30b6d06f2094c
Source dataset
uspto-grants-1994_03
Patent number
US05298492

Reaction notes

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