4-Nitrophenol → HCID 22216129, compound

HRID 129359Notes

Reaction equation

HRID 129359 reaction equation
[NH:1]([C:16]([O:18]C(C)(C)C)=O)[C@H:2]([C:10]([NH:12][CH2:13][C:14]#[N:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.FC(F)(F)[C:25]([O-:27])=[O:26].C(N([CH:36]([CH3:38])[CH3:37])CC)(C)C.O.O[N:41]1[C:45]2C=CC=CC=2N=N1.[CH:50]1C([N+]([O-])=O)=CC=C(O)C=1.C(N(CC)CCN)C>ClCCl.CN(C)C=O.C(OC(=O)C)C>[NH:41]([C:25]([O:27][C:36]([CH3:37])([CH3:38])[CH3:50])=[O:26])[CH2:45][C:16]([NH:1][C@H:2]([C:10]([NH:12][CH2:13][C:14]#[N:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:18]

Participants

10

Reactant 6

HCID 9804-NitrophenolHCID 60993N,N-DiethylethylenediamineHCID 81531Diisopropylethylamine2×HCID 84468TrifluoroacetateHCID 27960291-Hydroxybenzotriazole hydrateHCID 9904539HCID 9904539, compound

Product 1

HCID 22216129HCID 22216129, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ice-cold aqueous trifluoroacetic acid (10 ml) was added to a solution of Boc-L-Phe-NHCH2CN (5 mmol) in dichloromethane (10 ml). The reaction mixture was incubated at 20° C. for 30 minutes and then the solvent was removed by evaporation at 40° C. The residue was dissolved in chloroform, evaporated and the procedure repeated twice more. The resultant crude trifluoroacetate salt was dissolved in a solution of diisopropylethylamine (7.5 mmol) in dimethyl formamide (10 ml) and Boc-Gly-p-nitrophenyl ester (6.25 mmol) and N-hydroxybenzotriazole monohydrate (6.25 mmol) were added. Sufficient diisopropylethylamine was then added dropwise to generate p-nitrophenol (golden colour) and the mixture was stirred at room temperature for 2 hours. N,N-diethylethylenediamine (1.5 ml ) followed after 15 minutes by ethylacetate (60 ml) was added and the mixture was washed with water, aqueous triethylamine, water, aqueous potassium bisulphate, water, dried and evaporated. The residue was purified by chromatography on silica eluted with ethyl acetate:hexane (20:1) to yield Boc-Gly-L-Phe-NHCH2CN in the form of a foam.

Workup

  1. customthe solvent was removed by evaporation at 40° C
  2. dissolutionThe residue was dissolved in chloroform
  3. customevaporated
  4. additionwere added
  5. additionwas added
  6. washthe mixture was washed with water, aqueous triethylamine, water, aqueous potassium bisulphate, water
  7. customdried
  8. customevaporated
  9. customThe residue was purified by chromatography on silica
  10. washeluted with ethyl acetate:hexane (20:1)

Sources & evidence

ORD record
ord-596640656d98415e8b460867bb1dd97d
Source dataset
uspto-grants-1995_11
Patent number
US05468480

Reaction notes

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