Triphenylphosphine → HCID 178527237, compound

HRID 277128Notes

Reaction equation

HRID 277128 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[N:9]2[CH2:12][CH:11]([N:13]([CH2:17]C3C=C4C(=CC=3)N=CC=C4)[SH:14](=[O:16])=[O:15])[CH2:10]2)=[CH:4][CH:3]=1.ClC1C=CC(C(C2C=CC(Cl)=CC=2)N2CC(O)C2)=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:74]1[C:83]2[C:78](=[C:79](CNS(=O)=O)[CH:80]=[CH:81][CH:82]=2)[CH:77]=[CH:76][CH:75]=1.N(C(OCC)=O)=NC(OCC)=O.C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O1CCCC1>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]2[CH2:10][CH:11]([N:13]([CH2:17][C:79]3[CH:80]=[CH:81][CH:82]=[C:83]4[C:78]=3[CH:77]=[CH:76][CH:75]=[N:74]4)[SH:14](=[O:15])=[O:16])[CH2:12]2)=[CH:33][CH:32]=1

Participants

8

Reactant 6

HCID 11776TriphenylphosphineHCID 742671,2-Bis(diphenylphosphino)ethaneHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 218966141-[Bis(4-chlorophenyl)methyl]azetidin-3-olHCID 178527235HCID 178527235, compoundHCID 178527236HCID 178527236, compound

Product 1

HCID 178527237HCID 178527237, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

N-{1-[Bis(4-chlorophenyl)methyl]azetidin-3-yl}-N-quinol-6-ylmethylsulfonamide may be prepared by carrying out the procedure in the following manner: 0.70 g of 1-[bis(4-chlorophenyl)methyl]azetidin-3-ol and 0.597 g of triphenylphosphine are added, under argon, to a solution of 0.50 g of N-(quinol-5-yl)methylsulfonamide in 70 cm3 of anhydrous tetrahydrofuran and then 0.40 cm3 of diethyl azodicarboxylate and 0.45 g of 1,2-bis(diphenylphosphine)ethane are poured in. After stirring for 20 hours at 20° C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up in 70 cm3 of ethyl acetate, the resulting solution is washed with 30 cm3 of brine, dried over magnesium sulfate, filtered and then concentrated to dryness at 50° C. under reduced pressure (2.7 kPa). The violet oil obtained is purified by chromatography on a silica gel column (particle size 0.063-0.200 mm, height 35 cm, diameter 3.9 cm), eluting under an argon pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (40/60 then 30/70 and 20/80 by volume) and collecting 50-cm3 fractions. Fractions 6 to 12 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up in 15 cm3 of methanol, the resulting white suspension is filtered, the solid drained and then dried at 50° C. under reduced pressure (2.7 kPa). 0.35 g of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-N-quinol-5-ylmethylsulfonamide is obtained in the form of a white solid [1H NMR spectrum (300 MHz, CDCl3, δ in ppm): 2.60 (t, J=7 Hz: 1H); 2.84 (t, J=7 Hz: 1H); 2.99 (s: 3H); 3.36 (split t, J=7 and 2.5 Hz: 1H); 3.56 (split t, J=7 and 2.5 Hz: 1H); 4.01 (s: 1H); 4.85 (mt: 1H); from 7.10 to 7.25 (mt: 8H); 7.40 (dd, J=7.5 and 1 Hz: 1H); 7.54 (dd, J=8.5 and 4 Hz: 1H); 7.74 (dd, J=8 and 7.5 Hz: 1H); 8.20 (broad d, J=8 Hz: 1H); 8.54 (broad d, J=9 Hz: 1H); 8.99 (dd, J=4 and 1.5 Hz: 1H)].

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. washthe resulting solution is washed with 30 cm3 of brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness at 50° C. under reduced pressure (2.7 kPa)
  6. customThe violet oil obtained
  7. customis purified by chromatography on a silica gel column (particle size 0.063-0.200 mm, height 35 cm, diameter 3.9 cm)
  8. washeluting under an argon pressure of 0.5 bar
  9. additionwith a mixture of cyclohexane and ethyl acetate (40/60
  10. custom30/70 and 20/80 by volume) and collecting 50-cm3 fractions
  11. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  12. filtrationthe resulting white suspension is filtered
  13. customdried at 50° C. under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-f80bb3dbc509487f99896498cbc4827a
Source dataset
uspto-grants-2002_03
Patent number
US06355631B1

Reaction notes

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