HCID 86760498, compound → HCID 87713388, compound

HRID 1766906Notes

Reaction equation

HRID 1766906 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C@H:8]([C:16](=[O:23])[O:17]CC(Cl)(Cl)Cl)[CH2:9][C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])=[O:6])[CH:2]=[CH2:3]>C(O)(=O)C.[Zn]>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][C@H:8]([NH:7][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[C:16]([OH:23])=[O:17])[CH:14]=[CH2:15]

Participants

4

Reactant 1

HCID 86760498HCID 86760498, compound

Product 1

HCID 87713388HCID 87713388, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Allyl(S)-3-(allyloxycarbonylamino)-4-oxo-4-(2,2,2-trichloroethoxy)butyrate (350 mg, 9.02×10−4 mol) obtained from Example 20-(2) was dissolved in acetic acid (1.8 ml), then zinc powder (350 mg) was added thereto, and the resulting mixture was stirred at room temperature for 1 hour. The insoluble material was filtered off and washed with ethyl acetate. The filtrates were combined, and the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed successively with a 0.2N aqueous solution of hydrochloric acid and a saturated aqueous solution of sodium chloride. The resulting solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to afford the crude title compound (180 mg, 78% yield) as a pale yellow oil.

Workup

  1. filtrationThe insoluble material was filtered off
  2. washwashed with ethyl acetate
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution was washed successively with a 0.2N aqueous solution of hydrochloric acid
  6. dry with materialThe resulting solution was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8a38a2b32eb148e2a4059577eba227e6
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

Loading…