HCID 18639016, compound → HCID 18639008, compound

HRID 1588823Notes

Reaction equation

HRID 1588823 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-785fec670c514cefb16c5b2e0eb53a12
Source dataset
uspto-grants-1993_06
Patent number
US05223489

Reaction notes

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