Triphenylphosphine → (S)-Tert-butyl 2-(3'-chlorobiphenyl-4-yl)-1-(1-(2-cyanoethyl)-1H-tetrazol-5-yl)ethylcarbamate

HRID 333336Notes

Reaction equation

HRID 333336 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C@H:15]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:16]([NH:18][CH2:19][CH2:20][C:21]#[N:22])=O)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C[Si]([N:68]=[N+:69]=[N-:70])(C)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C@H:15]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:16]3[N:18]([CH2:19][CH2:20][C:21]#[N:22])[N:70]=[N:69][N:68]=3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 5363146Diisopropyl azodicarboxylateHCID 68748130(S)-Tert-butyl 3-(3'-chlorobiphenyl-4-yl)-1-(2-cyanoethylamino)-1-oxopropan-2-ylcarbamate

Product 1

HCID 68747779(S)-Tert-butyl 2-(3'-chlorobiphenyl-4-yl)-1-(1-(2-cyanoethyl)-1H-tetrazol-5-yl)ethylcarbamateYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-tert-butyl 3-(3′-chlorobiphenyl-4-yl)-1-(2-cyanoethylamino)-1-oxopropan-2-ylcarbamate (1.07 g, 2.500 mmol) in THF (50 ml) at room temperature was added Ph3P (1.640 g, 6.25 mmol), and the mixture was stirred at room temperature for 10 minutes. Then, to the mixture at 0° C. was added DIAD (1.215 ml, 6.25 mmol) and 2 minutes later was slowly added trimethylsilyl azide (0.828 ml, 6.25 mmol). The resulting light yellow suspension was slowly warmed up to room temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure. The obtained residue was purified by flash chromatography (silica gel, 25 to 50% EtOAc/Heptane) and gave the title compound: 423 mg (yield: 85%). LCMS (condition B): 453.2 (M+1); retention time=1.23 min.

Workup

  1. temperatureThe resulting light yellow suspension was slowly warmed up to room temperature
  2. stirringstirred overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe obtained residue was purified by flash chromatography (silica gel, 25 to 50% EtOAc/Heptane)

Sources & evidence

ORD record
ord-a6bf42e3a97e41debc9c3e08e4a2cc06
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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