Triphenylphosphine → HCID 54448135, compound

HRID 849872Notes

Reaction equation

HRID 849872 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][C@@H:8]([C:20](=O)[NH:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/[N:56]=[N:57]/C(OCC)=O)=O.C[Si]([N:67]=[N+]=[N-])(C)C.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[Ce]>C1COCC1.O>[C:1]([O:5][C:6](=[O:31])[NH:7][C@@H:8]([C:20]1[N:21]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:57]=[N:56][N:67]=1)[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 407333Cerate(2-), hexakis(nitrato-kappaO)-, potassium (1:2), (OC-6-11)-HCID 5462977Diethyl azodicarboxylateHCID 54217546HCID 54217546, compound

Product 1

HCID 54448135HCID 54448135, compoundYield 12.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

((1R)-2-(2-Naphthyl)-1-(phenethylcarbamoyl)ethyl)carbamic acid tert-butyl ester (2.20 g, 5.26 mmol) was dissolved in dry THF (50 ml). Triphenylphosphine (2.76 g; 10.52 mmol) diethylazodicarboxylate (1.66 g, 10.52 mmol) and trimethylsilyl azide (1.22 g; 10.52 mmol) were added. The mixture was stirred overnight at room temperature. Ammonium ceric nitrate (23.06 g; 21.04 mmol) was dissolved in water (400 ml) and added dropwise to the reation mixture. THF (120 ml) was added and the reaction mixture was extracted with methylene chloride (3×300 ml). The organic phase was dried (magnesium sulfate) and the solvent was removed in vacuo. The residue was chromatographed on silica (5×40 cm) using ethyl acetate/heptane as eluent (1:1) to afford 0.30 g of ((1R)-2-(2-naphthyl)-1-(1-phenethyl-1H-tetrazol-5-yl)ethyl)carbamic acid tert-butylester.

Workup

  1. additionadded dropwise to the reation mixture
  2. extractionthe reaction mixture was extracted with methylene chloride (3×300 ml)
  3. dry with materialThe organic phase was dried (magnesium sulfate)
  4. customthe solvent was removed in vacuo
  5. customThe residue was chromatographed on silica (5×40 cm)

Sources & evidence

ORD record
ord-63e3258fc2554dc3b9cc5fcde95cef8d
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

Loading…