Triphenylphosphine → HCID 178461790, compound

HRID 2368152Notes

Reaction equation

HRID 2368152 reaction equation
[CH:1]1([CH2:4][CH2:5][O:6][C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[C:9]([N+:15]([O-])=O)[CH:8]=2)[CH2:3][CH2:2]1.[N:18]([C@H:21]1[CH2:26][CH2:25][C@H:24]([O:27][CH2:28][C@@H:29]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH3:30])[CH2:23][CH2:22]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.P(OCC)(OCC)OCC>C1(C)C=CC=CC=1>[CH:1]1([CH2:4][CH2:5][O:6][C:7]2[CH:14]=[CH:13][C:10]3[C:9]([CH:8]=2)=[N:15][N:18]([C@H:21]2[CH2:26][CH2:25][C@H:24]([O:27][CH2:28][C@@H:29]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH3:30])[CH2:23][CH2:22]2)[CH:11]=3)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 31215Triethyl phosphiteHCID 57517513HCID 57517513, compoundHCID 178461791HCID 178461791, compound

Product 1

HCID 178461790HCID 178461790, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
160 °C

Procedure

A solution of 4-(2-cyclopropylethoxy)-2-nitrobenzaldehyde (0.79 g), tert-butyl {(1S)-2-[(trans-4-azidocyclohexyl)oxy]-1-methylethyl}carbamate (1.0 g), triphenylphosphine (3.08 g) and triethyl phosphite (3.08 g) in toluene (10 mL) was refluxed for 3 hr. The reaction mixture was allowed to cool, and concentrated under reduced pressure. To the obtained residue was added triethyl phosphite (4.0 g), and the mixture was stirred at 160° C. for 4 hr. The reaction mixture was allowed to cool, and purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (1.2 g).

Workup

  1. temperatureto cool
  2. concentrationconcentrated under reduced pressure
  3. additionTo the obtained residue was added triethyl phosphite (4.0 g)
  4. temperatureto cool
  5. custompurified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ad1e2875301a463a927cb7230ab3f360
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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