Triphenylphosphine → HCID 58941445, compound

HRID 747625Notes

Reaction equation

HRID 747625 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[N:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40][CH2:41][CH2:42]O)[CH:35]=1.[Cl:44][C:45]1[CH:50]=[CH:49][C:48]([NH:51][S:52]([C:55]2[CH:60]=[CH:59][C:58]([O:61][CH3:62])=[C:57]([O:63][CH3:64])[CH:56]=2)(=[O:54])=[O:53])=[C:47]([CH2:65][C:66]2[C:71]([F:72])=[CH:70][CH:69]=[CH:68][C:67]=2[F:73])[CH:46]=1>C1COCC1.C(OCC)C>[Cl:44][C:45]1[CH:50]=[CH:49][C:48]([N:51]([CH2:42][CH2:41][CH2:40][C:36]2[CH:35]=[N:34][CH:39]=[CH:38][CH:37]=2)[S:52]([C:55]2[CH:60]=[CH:59][C:58]([O:61][CH3:62])=[C:57]([O:63][CH3:64])[CH:56]=2)(=[O:53])=[O:54])=[C:47]([CH2:65][C:66]2[C:71]([F:72])=[CH:70][CH:69]=[CH:68][C:67]=2[F:73])[CH:46]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 178613-PyridinepropanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 68564783HCID 68564783, compound

Product 1

HCID 58941445HCID 58941445, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 1.5 g of triphenylphosphine dissolved in 25 ml of THF is added 0.909 g of diisopropyl azodicarboxylate. After 15 minutes at room temperature, 0.61 g of 3-pyrid-3-ylpropan-1-ol is introduced and the mixture is left at 20° C. for 15 minutes. 1.36 g of N-[4-chloro-2-(2,6-difluorobenzyl)phenyl]-3,4-dimethoxybenzenesulfonamide are introduced and the mixture is left at room temperature for 18 hours. The medium is concentrated and the residue is chromatographed on a column of silica gel, eluting with a toluene/ethyl acetate mixture passing from a ratio of 9/1 to 5/5 (v/v). 5 ml of 2M hydrochloric acid are added to the product obtained, dissolved in diethyl ether, and the solvents are then evaporated off. The residue is taken up in diisopropyl ether to give, after filtration, 0.55 g of the expected product.

Workup

  1. waitthe mixture is left at 20° C. for 15 minutes
  2. waitthe mixture is left at room temperature for 18 hours
  3. concentrationThe medium is concentrated
  4. customthe residue is chromatographed on a column of silica gel
  5. washeluting with a toluene/ethyl acetate mixture
  6. addition5 ml of 2M hydrochloric acid are added to the product
  7. customobtained
  8. customthe solvents are then evaporated off
  9. customto give
  10. filtrationafter filtration, 0.55 g of the expected product

Sources & evidence

ORD record
ord-ec5faf924d4c4588b091cb6650a304c1
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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