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Pyridine → ethyl gamma-(N-carbobenzoxy)amino-gamma-cyanobutanoate

HRID 1648503
Notes
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Reaction equation

HRID 1648503 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6](=C=O)[C@@H:7]([C:19](=O)[NH2:20])[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[CH3:2].N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCCC1>[C:9]([NH:8][CH:7]([C:19]#[N:20])[CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:24])([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 131716763HCID 131716763, compound

Product 1

HCID 53725343ethyl gamma-(N-carbobenzoxy)amino-gamma-cyanobutanoateYield 79.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 21.45 g of N-carbobenzoxy-carbonyl-L-isoglutamine ethyl ester in 200 mL of dry tetrahydrofuran kept at 0° C. to -5° C. in an ice-bath 11.82 mL of pyridine is added. To the above solution 9.84 mL of trifluoroacetic anhydride in 100 mL of tetrahydrofuran is added dropwise at such a rate that the bath temperature is maintained. The solution is stirred for 2 hours at this temperature. The solution is evaporated to dryness and the oil is dissolved in ethyl acetate. The organic layer is washed with 1.0N hydrochloric acid and sterile water. The solution is dried and evaporated in vacuo to give; an oil to give 14.8 g of ethyl γ-(N-carbobenzoxy)amino-γ-cyanobutanoate, 17.

Workup

  1. customkept at 0° C. to -5° C. in an ice-bath
  2. temperatureis maintained
  3. customThe solution is evaporated to dryness
  4. dissolutionthe oil is dissolved in ethyl acetate
  5. washThe organic layer is washed with 1.0N hydrochloric acid and sterile water
  6. customThe solution is dried
  7. customevaporated in vacuo
  8. customto give

Sources & evidence

ORD record
ord-ecf2c3d88e304d389a6fd4f3aba78697
Source dataset
uspto-grants-1995_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05436352

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes