tert-Butanol → HCID 86665962, compound
Reaction equation
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]2[CH:9]=[C:10]([CH:14]=[C:15]([O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=3)[CH:16]=2)C(O)=O)=[CH:5][CH:4]=1)#[N:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:35])C=CC=CC=1.CC[N:47]([CH:51](C)C)C(C)C.[C:54]([OH:58])([CH3:57])([CH3:56])[CH3:55]>>[C:54]([O:58][C:51](=[O:35])[NH:47][C:10]1[CH:14]=[C:15]([O:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[CH:22][CH:23]=2)[CH:16]=[C:8]([O:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:27][CH:26]=2)[CH:9]=1)([CH3:57])([CH3:56])[CH3:55]Participants
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 3,5-bis-(4-cyano-phenoxy)-benzoic acid (2.0 g, 5.6 mmol), diphenylphosphorylazide (1.2 ml, 5.6 mmol) and DIPEA (1 ml, 5.6 mmol) were dissolved in 20 ml of tert-butanol and stirred overnight at 80° C. Reaction mixture was cooled and diluted with 50 ml saturated solution of sodiumhydrogencarbonate and extracted with ethylacetate (3×50 ml). Combined organic layer was washed with 2×50 ml saturated solution of brineand dried over anhydrous sodium sulphate. Solvent was evaporated under vacuo and thus obtained crude product was subjected to column chromatography using silica gel as an absorbent and eluted with 10-20% mixture of ethylacetate and hexane to afford 1.0 g of the required product. Percentage purity (LCMS): 89.6%, (M+1)=427.1+1.
Workup
- customReaction mixture
- temperaturewas cooled
- extractionextracted with ethylacetate (3×50 ml)
- washCombined organic layer was washed with 2×50 ml saturated solution of brineand
- dry with materialdried over anhydrous sodium sulphate
- customSolvent was evaporated under vacuo
- customthus obtained crude product
- washeluted with 10-20% mixture of ethylacetate and hexane
Sources & evidence
- ORD record
- ord-be81042fbf7e43a7bf304e4ca095246d
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722930B2
Reaction notes
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