Triphenylphosphine → HCID 59607591, compound

HRID 70867Notes

Reaction equation

HRID 70867 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH2:5][C@H:6]([NH:20][C:21](=[O:31])[CH2:22][CH2:23][C:24](=O)[NH:25][CH2:26][CH2:27][C:28]#[N:29])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[CH3:2].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:70]=[N+:71]=[N-:72])(C)C>C1COCC1>[CH2:1]([O:3][C:4](=[O:32])[CH2:5][C@H:6]([NH:20][C:21](=[O:31])[CH2:22][CH2:23][C:24]1[N:25]([CH2:26][CH2:27][C:28]#[N:29])[N:72]=[N:71][N:70]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:10][CH:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 5363146Diisopropyl azodicarboxylateHCID 67208765(R)-4-biphenyl-4-yl-3-[3-(2-cyano-ethylcarbamoyl)-propionylamino]-butyric acid ethyl ester

Product 1

HCID 59607591HCID 59607591, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Next, to a solution of (R)-4-biphenyl-4-yl-3-[3-(2-cyano-ethylcarbamoyl)-propionylamino]-butyric acid ethyl ester (204 mg, 0.468 mmol) in THF (10 mL) at room temperature is added Ph3P (307 mg, 1.17 mmol) and the mixture is stirred at room temperature for 10 minutes. Then to the mixture at ice bath temperature is added DIAD (0.228 ml, 1.171 mmol) and trimethylsilyl azide (0.155 ml, 1.171 mmol). The resulting mixture is slowly warmed up to room temperature and stirred for 16 hours. The reaction mixture is concentrated under reduced pressure. The obtained residue is purified by flash chromatography (silica gel, 1% to 3% EtOH/DCM) to give (R)-4-biphenyl-4-yl-3-{3-[1-(2-cyano-ethyl)-1H-tetrazol-5-yl]-propionylamino}-butyric acid ethyl ester (137 mg, 64% yield). HPLC retention time=1.61 minutes (condition C); MS=461 (m+1).

Workup

  1. temperatureThe resulting mixture is slowly warmed up to room temperature
  2. stirringstirred for 16 hours
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. customThe obtained residue is purified by flash chromatography (silica gel, 1% to 3% EtOH/DCM)

Sources & evidence

ORD record
ord-1b00ac46c7e84f29aa337fddd167041d
Source dataset
uspto-grants-2014_09
Patent number
US08822534B2

Reaction notes

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