Triphenylphosphine → HCID 59829670, compound

HRID 551136Notes

Reaction equation

HRID 551136 reaction equation
[N:1]([CH:4]([C:25]1[O:29][C:28]([CH2:30][N:31]([CH3:33])[CH3:32])=[CH:27][CH:26]=1)[CH2:5][C:6]1[C:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:14]2[C:9]([CH:10]=[CH:11][CH:12]=[N:13]2)=[C:8]([Cl:24])[CH:7]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O.C(OCC)(=O)C>[CH2:17]([O:16][C:15]1[C:6]([CH2:5][CH:4]([C:25]2[O:29][C:28]([CH2:30][N:31]([CH3:32])[CH3:33])=[CH:27][CH:26]=2)[NH2:1])=[CH:7][C:8]([Cl:24])=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 2

HCID 11776TriphenylphosphineHCID 59829664HCID 59829664, compound

Product 1

HCID 59829670HCID 59829670, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a stirring solution of 1-(5-{1-azido-2-[8-(benzyloxy)-5-chloroquinolin-7-yl]ethyl}-2-furyl)-N,N-dimethylmethanamine (0.1.451 mmol) in tetrahydrofuran (5 mL) and water (1.5 mL) in a round bottom flask equipped with a reflux condenser was added triphenylphosphine (1.596 mmol, 1.1 eq.) (CAUTION: vigorous gas evolution, do not seal reaction vessel) and the resulting mixture was then warmed to 70° C. and stirred 2 h. The reaction mixture was then allowed to cool to room temperature, diluted with ethyl acetate (50 mL) and was washed with 1N HCl (3×25 mL). The aqueous layers were combined, backextracted with ethyl acetate (25 mL) and then adjusted to pH=12 by addition of 5N NaOH resulting in a precipitate. The aqueous solution was extracted with ethyl acetate (3×50 mL) and the organic layers were combined, dried (MgSO4), filtered and concentrated a yellow oil that was used directly in the ensuing step. MS (ESI) m/z 436.4; HRMS: calcd for C25H26ClN3O2+H+, 436.17863; found (ESI, [M+H]+ Obs'd), 436.1788.

Workup

  1. customvigorous gas evolution, do not seal
  2. customreaction vessel) and the resulting mixture
  3. temperatureto cool to room temperature
  4. washwas washed with 1N HCl (3×25 mL)
  5. additionadjusted to pH=12 by addition of 5N NaOH resulting in a precipitate
  6. extractionThe aqueous solution was extracted with ethyl acetate (3×50 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated a yellow oil that

Sources & evidence

ORD record
ord-c628f36868804454be5d0fd55044bfdb
Source dataset
uspto-grants-2011_05
Patent number
US07947712B2

Reaction notes

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