Triphenylphosphine → HCID 69707452, compound

HRID 2414376Notes

Reaction equation

HRID 2414376 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([NH:23][CH2:24][CH2:25][C:26]#[N:27])=O)[CH:16]=1)[C:10]#[N:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C[Si]([N:65]=[N+:66]=[N-:67])(C)C>C(#N)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[N:23]([CH2:24][CH2:25][C:26]#[N:27])[N:67]=[N:66][N:65]=2)[CH:16]=1)[C:10]#[N:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 78378AzidotrimethylsilaneHCID 69708688HCID 69708688, compound

Product 1

HCID 69707452HCID 69707452, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of (S)-2-t-butoxycarbonylamino-3-[3-(2-cyanoethylaminocarbonyl)-benzyloxy]-propionitrile (3.8 g, 10.2 mmol) and triphenylphosphine (6.7 g, 25.5 mmol) in acetonitrile (75 mL) at 0° C. is added diisopropyl azodicarboxylate (5.0 mL, 25.5 mmol) and trimethylsilyl azide (3.73 mL, 28.1 mmol) dropwise, simultaneously, via syringe. The solution is then stirred at room temp. for 0.5 h, and then heated to 30° C. overnight. After solvent evaporation, the residue is taken up in EtOAc (150 mL), and then poured onto an ice—sat'd NaHCO3 mixture (150 mL), and extracted. The organic phase is washed with brine (100 mL), dried (MgSO4), evaporated and chromatographed (silica, 65% EtOAc/hexane) to yield (S)-2-t-butoxycarbonylamino-3-{3-[1-(2-cyanoethyl)-5-tetrazolyl]-benzyloxy}-propionitrile, as a light yellow oil.

Workup

  1. customAfter solvent evaporation
  2. additionpoured onto an ice—
  3. extractionextracted
  4. washThe organic phase is washed with brine (100 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customchromatographed (silica, 65% EtOAc/hexane)

Sources & evidence

ORD record
ord-f86b51ea820642158a618800599de80f
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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