Triphenylphosphine → HCID 86630730, compound

HRID 547823Notes

Reaction equation

HRID 547823 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:79])([F:78])[C:34]1[CH:35]=[C:36]([C:44]([CH3:77])([CH3:76])[C:45]([N:47]([C:49]2[CH:50]=[N:51][C:52]([NH:63][CH:64]([CH2:74][OH:75])[CH2:65][O:66][Si:67]([C:70]([CH3:73])([CH3:72])[CH3:71])([CH3:69])[CH3:68])=[CH:53][C:54]=2[C:55]2[CH:60]=[CH:59][C:58]([F:61])=[CH:57][C:56]=2[CH3:62])[CH3:48])=[O:46])[CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=1.[C:80](O)(=[S:82])[CH3:81]>C1COCC1>[F:79][C:33]([F:32])([F:78])[C:34]1[CH:35]=[C:36]([C:44]([CH3:77])([CH3:76])[C:45]([N:47]([CH3:48])[C:49]2[C:54]([C:55]3[CH:60]=[CH:59][C:58]([F:61])=[CH:57][C:56]=3[CH3:62])=[CH:53][C:52]([NH:63][CH:64]([CH2:65][O:66][Si:67]([C:70]([CH3:72])([CH3:73])[CH3:71])([CH3:68])[CH3:69])[CH2:74][O:75][C:80](=[S:82])[CH3:81])=[N:51][CH:50]=2)=[O:46])[CH:37]=[C:38]([C:40]([F:42])([F:43])[F:41])[CH:39]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86630731HCID 86630731, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86630730HCID 86630730, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.19 mg (0.71 mmol) triphenylphosphine in 10 ml dry THF were added 0.12 g (0.71 mmol) diethyl azodicarboxylate at 0° C. under argon. After 30 min a solution of 0.50 g (0.71 mmol) (RS)-2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-[2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxymethyl-ethylamino]-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide in 5 ml dry THF and 0.06 g (0.9 mmol) thioacetic acid were added. The reaction mixture was allowed to warm to room temperature over night. Dilution with a saturated aqueous solution of sodium hydrogencarbonate was followed by extraction with three portions of tert-butyl methyl ether. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Flash column chromatography gave 0.28 g (52%) of the title compound as a white solid.

Workup

  1. extractionDilution with a saturated aqueous solution of sodium hydrogencarbonate was followed by extraction with three portions of tert-butyl methyl ether
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ee2b46486c44ca290b9e104d846f068
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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