HCID 54517925, compound → HCID 54536021, compound

HRID 1282591Notes

Reaction equation

HRID 1282591 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C@H:4]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=1)[NH:5][C:6]([C:8]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7]>C(O)C>[CH3:1][O:2][C:3](=[O:29])[C@H:4]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([NH2:26])=[CH:24][CH:25]=1)[NH:5][C:6]([C:8]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7]

Participants

3

Reactant 1

HCID 54517925HCID 54517925, compound

Product 1

HCID 54536021HCID 54536021, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of N-[(1-phenylcyclopentyl)carbonyl]-4-nitro-L-phenylalanine methyl ester (3.5 g, 8.88 mmol) and stannous chloride (10 g, 44 mmol) in 60 mL of ethanol was refluxed for 50 min under argon. The ethanol was then removed under reduced pressure and the residue was treated with 50 mL of saturated NaHCO3 followed by sodium carbonate to adjust pH above 9. The white slurry was extracted with ethyl acetate (3×300 mL). The combined extracts were washed with water (100 mL) and brine (100 mL) and were dried (MgSO4). Removal of the solvent afforded 4-amino-N-[(1-phenylcyclopentyl)carbonyl]-L-phenylalanine methyl ester (2.9 g, 89%).

Workup

  1. temperaturewas refluxed for 50 min under argon
  2. customThe ethanol was then removed under reduced pressure
  3. additionthe residue was treated with 50 mL of saturated NaHCO3
  4. extractionThe white slurry was extracted with ethyl acetate (3×300 mL)
  5. washThe combined extracts were washed with water (100 mL) and brine (100 mL)
  6. dry with materialwere dried (MgSO4)
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-2d41fd1d83b24049954694c319945c7d
Source dataset
uspto-grants-2002_09
Patent number
US06455550B1

Reaction notes

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