Triphenylphosphine → HCID 131734986, compound

HRID 923484Notes

Reaction equation

HRID 923484 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:11]([NH:13][CH2:14][CH2:15][C:16]#[N:17])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.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:63]=[N+:64]=[N-:65])(C)C>C(#N)C>[CH2:1]([O:8][CH2:9][C@H:10]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:11]1[N:13]([CH2:14][CH2:15][C:16]#[N:17])[N:65]=[N:64][N:63]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 78378AzidotrimethylsilaneHCID 131734987HCID 131734987, compound

Product 1

HCID 131734986HCID 131734986, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 410 mg of tert-butyl {(2S)-3-(benzyloxy)-1-[(2-cyanoethyl)amino]-1-oxopropan-2-yl}carbamate, 400 mg of triphenylphosphine, and 10 ml of acetonitrile were added 310 μl of diisopropyl azodicarboxylate and 210 μl of trimethylsilyl azide under ice-cooling, followed by stirring at room temperature for 22 hours. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 280 mg of tert-butyl {(1R)-2-(benzyloxy)-1-[1-(2-cyanoethyl)-1H-tetrazol-5-yl]ethyl}carbamate.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f0123a34cbe0467f82d7a1b5ce01bfcb
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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