Benzene → HCID 53921152, compound

HRID 1799442Notes

Reaction equation

HRID 1799442 reaction equation
C(O[C:9]([NH:11][C@H:12](C(O)=O)[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=O)C1C=CC=CC=1.[CH2:21]=[O:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>C(O)(=O)C.ClCCl.C(OCC)(=O)C.CO.ClCCl>[O:22]1[CH2:21][CH2:9][NH:11][CH:12]1[CH2:13][CH2:14][C:15]([OH:17])=[O:16]

Participants

9

Reactant 4

HCID 241BenzeneHCID 712FormaldehydeHCID 70866L-Glutamic acid, N-((phenylmethoxy)carbonyl)-HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 53921152HCID 53921152, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Into a 250 mL round bottomed flask equipped with an Dean-Stark distilling trap was charged 8 g (28.4 mmole) of N-benzyloxycarbonyl-L-glutamic acid, 1.45 g (50 mmole) paraformaldehyde, 28.5 mg p-toluenesulfonic acid monohydrate and 150 mL benzene. The mixture was refluxed for 8 hr during which the solution turned yellowish in color and solid appeared in the condenser and trap. Evaluation with TLC (silica gel GF, solvent: 5% methanol/dichloromethane or ethyl acetate:dichloromethane:acetic acid=1:1:0.05) indicated the reaction was complete. The reaction mixture was cooled down to room temperature, and then rotary evaporated to dryness. The residue was taken into ethyl acetate and washed with benzene. The ethyl acetate solution was dried over magnesium sulfate, filtered, and concentrated to yield the oxazolidine propionic acid product (quantitative recovery)

Workup

  1. customInto a 250 mL round bottomed flask equipped with an Dean-Stark
  2. distillationdistilling trap
  3. temperatureThe mixture was refluxed for 8 hr during which the solution
  4. customrotary evaporated to dryness
  5. washwashed with benzene
  6. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1993aa9f4acd478594a5ec9d40a6db2d
Source dataset
uspto-grants-2013_01
Patent number
US08344115B2

Reaction notes

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