Triphenylphosphine → HCID 118223437, compound

HRID 2200179Notes

Reaction equation

HRID 2200179 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:14])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].O[CH:16]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OCC)=O)=NC(OCC)=O.C([O-])(O)=O.[Na+]>C1COCC1.O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1)[O:14][CH:16]1[CH2:17][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19]1)([O-:3])=[O:2]

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 516892Sodium BicarbonateHCID 27562513-Hydroxy-5-nitrobenzotrifluorideHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 118223437HCID 118223437, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 3-nitro-5-(trifluoromethyl)phenol (500 mg, 2.4 mmol), tert-butyl 3-hydroxyazetidine-1-carboxylate (500 mg, 2.9 mmol), PPh3 (9.5 g, 3.6 mmol) in THF (8 mL) and cool to 0° C. on ice bath. Add slowly diethyl azodicarboxylate (630 mg, 3.6 mmol). Stir the mixture at 35° C. for 16 hrs. Pour the mixture into water (50 mL), adjust pH to neutral with saturated NaHCO3 solution. Extract with EtOAc (15 mL×3), combine the organic layers; wash with brine (100 mL), dry over anhydrous Na2SO4. Concentrate under reduced pressure to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=15:85) affords the target compound (760 mg, 87%).

Workup

  1. extractionExtract with EtOAc (15 mL×3)
  2. washwash with brine (100 mL)
  3. dry with materialdry over anhydrous Na2SO4
  4. concentrationConcentrate under reduced pressure
  5. customto give the crude product
  6. customPurification by chromatography (silica gel, EtOAc:PE=15:85)

Sources & evidence

ORD record
ord-a05e1ace87e54d7c9fc0dee7349b08bd
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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