Triphenylphosphine → HCID 86630728, compound

HRID 547816Notes

Reaction equation

HRID 547816 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[F:32][C:33]([F:73])([F:72])[C:34]1[CH:35]=[C:36]([C:44]([CH3:71])([CH3:70])[C:45]([N:47]([C:49]2[C:50]([C:62]3[CH:67]=[CH:66][C:65]([F:68])=[CH:64][C:63]=3[CH3:69])=[CH:51][C:52]([N:55]3[CH2:60][CH2:59][CH:58]([OH:61])[CH2:57][CH2:56]3)=[N:53][CH:54]=2)[CH3:48])=[O:46])[CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=1.[C:74](O)(=[S:76])[CH3:75]>C1COCC1>[F:73][C:33]([F:32])([F:72])[C:34]1[CH:35]=[C:36]([C:44]([CH3:70])([CH3:71])[C:45]([N:47]([CH3:48])[C:49]2[C:50]([C:62]3[CH:67]=[CH:66][C:65]([F:68])=[CH:64][C:63]=3[CH3:69])=[CH:51][C:52]([N:55]3[CH2:60][CH2:59][CH:58]([O:61][C:74](=[S:76])[CH3:75])[CH2:57][CH2:56]3)=[N:53][CH:54]=2)=[O:46])[CH:37]=[C:38]([C:40]([F:41])([F:42])[F:43])[CH:39]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86630729HCID 86630729, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86630728HCID 86630728, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.22 g (0.84 mmol) triphenylphosphine and 0.15 g (0.84 mmol) diethyl azodicarboxylate in 3.33 ml THF was stirred for 15 min at 0° C. This solution was added to a solution of 0.25 g (0.42 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[4′-(4-fluoro-2-methyl-phenyl)-4-hydroxy-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-yl]-N-methyl-isobutyramide and 64 mg (0.84 mmol) thioacetic acid in 10 ml THF at 0° C. Conversion was monitored by thin layer chromatography. After complete consumption of the starting material a 2 N aqueous solution of sodium carbonate was added. The mixture was extracted with three portions of tert-butyl methyl ether. The combined organic extracts were dried over sodium sulphate and concentrated. Flash column chromatography gave 0.16 g (59%) of the title compound as a white solid.

Workup

  1. customAfter complete consumption of the starting material a 2 N aqueous solution of sodium carbonate
  2. additionwas added
  3. extractionThe mixture was extracted with three portions of tert-butyl methyl ether
  4. dry with materialThe combined organic extracts were dried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e53ebf7c61e042689c04f6cab1e32816
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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