tert-Butanol → HCID 136173745, compound

HRID 1698746Notes

Reaction equation

HRID 1698746 reaction equation
[CH3:1][N:2]([CH3:45])[C:3]([CH2:5][O:6][C:7]1[C:8]([F:44])=[C:9]([CH:15]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]3[N:42]=[C:41]([CH3:43])[O:40][N:39]=3)=[CH:34][CH:33]=2)[C:16]2[NH:20][C:19](=[O:21])[N:18]([C:22]3[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=3C(O)=O)[N:17]=2)[CH:10]=[C:11]([CH2:13][CH3:14])[CH:12]=1)=[O:4].C([N:48]([CH2:51]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:60])C=CC=CC=1.C(OCC)(=O)C.[C:76]([OH:80])([CH3:79])([CH3:78])[CH3:77]>O>[C:76]([O:80][C:51](=[O:60])[NH:48][C:23]1[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=1[N:18]1[C:19](=[O:21])[NH:20][C:16]([CH:15]([C:9]2[CH:10]=[C:11]([CH2:13][CH3:14])[CH:12]=[C:7]([O:6][CH2:5][C:3](=[O:4])[N:2]([CH3:45])[CH3:1])[C:8]=2[F:44])[NH:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]3[N:42]=[C:41]([CH3:43])[O:40][N:39]=3)=[CH:34][CH:33]=2)=[N:17]1)([CH3:79])([CH3:78])[CH3:77]

Participants

7

Reactant 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 136173790HCID 136173790, compound

Product 1

HCID 136173745HCID 136173745, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.320 g of 2-(3-{(3-dimethylcarbamoylmethoxy-5-ethyl-2-fluorophenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-1-yl)benzoic acid, 0.098 ml of triethylamine and 0.151 ml of diphenylphosphorylazide in 10 ml of t-butanol was stirred under a nitrogen atmosphere at room temperature for 20 hours and then at 70° C. for 36 hours. After adding 100 ml of ethyl acetate and 50 ml of water to the reaction mixture, the organic layer was dried over anhydrous magnesium sulfate, the desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methanol-ethyl acetate) to give the title compound (0.135 g) as a white solid.

Workup

  1. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  2. filtrationthe desiccating agent was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (methanol-ethyl acetate)

Sources & evidence

ORD record
ord-7059350a6e6e45d191e334a637f9dd96
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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