Triphenylphosphine → HCID 10753283, compound

HRID 2396995Notes

Reaction equation

HRID 2396995 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@@H:12](O)[CH3:13])[CH2:11][O:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:34]1[CH:38]=[N:37][N:36]=[N:35]1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@H:12]([N:35]2[N:36]=[N:37][CH:38]=[N:34]2)[CH3:13])[CH2:11][O:10]1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanolHCID 178418441HCID 178418441, compound

Product 1

HCID 10753283HCID 10753283, compoundYield 69.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (200 mg) in tetrahydrofuran (5 ml) were added triphenylphosphine (787 mg), tetrazole (210 mg) and diethyl azodicarboxylate (0.47 ml) at 0° C. under argon atmosphere. The mixture was stirred for 16 hours at room temperature. To the reaction mixture were added ethyl acetate (30 ml) and water (15 ml). The separated aqueous layer was extracted with ethyl acetate (20 ml). The combined organic layers were washed with water and saturated saline, dried (MgSO4) and concentrated. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4:1→3:1→2:1) to give (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-(2H-tetrazol-2-yl)ethyl]oxirane (176 mg).

Workup

  1. extractionThe separated aqueous layer was extracted with ethyl acetate (20 ml)
  2. washThe combined organic layers were washed with water and saturated saline
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4:1→3:1→2:1)

Sources & evidence

ORD record
ord-22527d4cf97a4d13ace74bf849766f08
Source dataset
uspto-grants-1996_02
Patent number
US05495024

Reaction notes

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