HCID 18639016, compound → HCID 18639008, compound

HRID 1649911Notes

Reaction equation

HRID 1649911 reaction equation
[CH3:1][N:2]([C:17]([O:19][C@@H:20]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])=[O:18])[CH2:3][CH2:4][C:5]([O:7]CC(C1C=CC=CC=1)=O)=[O:6]>C(O)(=O)C.[Zn]>[CH3:1][N:2]([C:17]([O:19][C@@H:20]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])=[O:18])[CH2:3][CH2:4][C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 18639016HCID 18639016, compound

Product 1

HCID 18639008HCID 18639008, compoundYield 70.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

To a solution of benzyl 2(S)-[N-methyl-N-(2-phenacyloxycarbonylethyl)aminocarbonyloxy]-3-phenylpropionate (1.0 g) in acetic acid (10 ml) was added zinc dust (1.0 g) portionwise at ambient temperature. After being stirred for 2 hours, zinc dust (0.2 g) was added thereto. The reaction mixture was stirred overnight at the same temperature and filtered, and the filtrate was evaporated in vacuo. The residue was dissolved in ethyl acetate (30 ml) and 0.5N hydrochloric acid (30 ml). The organic layer was extracted with 1N sodium hydroxide solution (20 ml×3). The combined aqueous extract was acidified to pH 2 with 1N hydrochloric acid and extracted with chloroform (50 ml ×3). The extract was washed with brine and dried over magnesium sulfate. Evaporation of the solvent gave benzyl 2(S)-[N-methyl-N-(2-carboxyethyl)aminocarbonyloxy]-3-phenylpropionate (543 mg) as an oil.

Workup

  1. stirringThe reaction mixture was stirred overnight at the same temperature
  2. filtrationfiltered
  3. customthe filtrate was evaporated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (30 ml)
  5. extractionThe organic layer was extracted with 1N sodium hydroxide solution (20 ml×3)
  6. extractionThe combined aqueous extract
  7. extractionextracted with chloroform (50 ml ×3)
  8. washThe extract was washed with brine
  9. dry with materialdried over magnesium sulfate
  10. customEvaporation of the solvent

Sources & evidence

ORD record
ord-bc56733242954d0f9ee94af63230825d
Source dataset
uspto-grants-1990_05
Patent number
US04921855

Reaction notes

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