Triphenylphosphine → HCID 19094408, compound

HRID 487236Notes

Reaction equation

HRID 487236 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([NH:13][CH2:14][CH2:15][C:16]#[N:17])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C[Si]([N:53]=[N+:54]=[N-:55])(C)C>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[N:13]([CH2:14][CH2:15][C:16]#[N:17])[N:55]=[N:54][N:53]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 78378Azidotrimethylsilane2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 19094330HCID 19094330, compound

Product 1

HCID 19094408HCID 19094408, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-(t-butoxycarbonylamino)-N-(2-cyanoethyl)propionamide (4.6 mmol) in THF (40 mL) under nitrogen is added triphenylphosphine (4.6 mmol). The solution is cooled to 0° and treated with diethyl azodicarboxylate (DEAD, 2.4 mmol) followed by trimethylsilyl azide (2.4 mmol). The solution is warmed up to room temperature and stirred for 18 hours. One additional equivalent of triphenyl phosphine (4.6 mmol), DEAD (2.4 mmol) and trimethylsilyl azide (2.4 mmol) are added and stirring is continued for 3 days. The solution is cooled to 0°. Ceric ammonium nitrate (0.2 L; 10% aqueous solution) is added dropwise. After 20 minutes of stirring, extraction is carried out with methylene chloride. The organic extract is dried over anhydrous sodium sulfate, then concentrated in vacuo. The residue is purified by chromatography to give 3-[5-(2-t-butoxycarbonylamino-ethyl)-tetrazol-1-yl]propionitrile.

Workup

  1. temperatureThe solution is cooled to 0°
  2. stirringstirring
  3. waitis continued for 3 days
  4. temperatureThe solution is cooled to 0°
  5. stirringAfter 20 minutes of stirring
  6. extractionextraction
  7. extractionThe organic extract
  8. dry with materialis dried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-70beb4f50ad246379e195ae3debc3551
Source dataset
uspto-grants-1994_03
Patent number
US05294632

Reaction notes

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