Triphenylphosphine → tert-Butyl 2-{4-[5-(2-fluorophenoxy)oxazolo[5,4-b]pyridin-2-yl]-2,6-dimethylphenoxy}-2-methylpropionate

HRID 2039765Notes

Reaction equation

HRID 2039765 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]1[CH:57]=[CH:56][CH:55]=[CH:54][C:34]=1[O:35][C:36]1[N:41]=[C:40]2[O:42][C:43]([C:45]3[CH:50]=[C:49]([CH3:51])[C:48]([OH:52])=[C:47]([CH3:53])[CH:46]=3)=[N:44][C:39]2=[CH:38][CH:37]=1.O[C:59]([CH3:68])([CH3:67])[C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61]>O1CCCC1.C(N(CC)CC)C>[F:32][C:33]1[CH:57]=[CH:56][CH:55]=[CH:54][C:34]=1[O:35][C:36]1[N:41]=[C:40]2[O:42][C:43]([C:45]3[CH:50]=[C:49]([CH3:51])[C:48]([O:52][C:59]([CH3:68])([CH3:67])[C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])=[C:47]([CH3:53])[CH:46]=3)=[N:44][C:39]2=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 11776Triphenylphosphine2×HCID 118940tert-Butyl 2-hydroxyisobutyrateHCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 1364132384-[5-(2-Fluorophenoxy)oxazolo[5,4-b]pyridin-2-yl]-2,6-dimethylphenol

Product 1

HCID 71204480tert-Butyl 2-{4-[5-(2-fluorophenoxy)oxazolo[5,4-b]pyridin-2-yl]-2,6-dimethylphenoxy}-2-methylpropionate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

With ice cooling, 72 mg of triphenylphosphine were dissolved in 1 ml of dry tetrahydrofuran, and 47 mg of diethyl azodicarboxylate were added. After 15 min, 80 mg of 4-[5-(2-fluorophenoxy)oxazolo[5,4-b]pyridin-2-yl]-2,6-dimethylphenol were added, followed by 32 μl of triethylamine and 44 mg of tert-butyl alpha-hydroxyisobutyrate. The reaction mixture was then stirred at room temperature for 16 hours, and another 72 mg of triphenylphosphine and 47 mg of diethyl azodicarboxylate were added with ice cooling. After a further 4 h at room temperature, the reaction was concentrated and purified by preparative HPLC. This gave 60 mg (53%) of the title compound.

Workup

  1. waitAfter a further 4 h at room temperature
  2. concentrationthe reaction was concentrated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f8cfbaf7b8b4454684fd29f9c0eebaa8
Source dataset
uspto-grants-2013_11
Patent number
US08580816B2

Reaction notes

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