tert-Butanol → HCID 178452692, compound

HRID 491814Notes

Reaction equation

HRID 491814 reaction equation
C([C:4]1[C:9]2[C:10]([NH:23][C:24]([C@H:26]3[CH2:31][CH2:30][C@H:29]([N:32]4[CH2:36][CH2:35][CH2:34][C:33]4=[O:37])[CH2:28][CH2:27]3)=[O:25])=[C:11]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=3)=[O:14])[O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)(O)=O.C([N:40]([CH2:43]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:52])C=CC=CC=1.[C:62]([OH:66])([CH3:65])([CH3:64])[CH3:63]>C(=O)([O-])O.[Na+]>[C:62]([O:66][C:43]([NH:40][C:4]1[C:9]2[C:10]([NH:23][C:24]([C@H:26]3[CH2:27][CH2:28][C@H:29]([N:32]4[CH2:36][CH2:35][CH2:34][C:33]4=[O:37])[CH2:30][CH2:31]3)=[O:25])=[C:11]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=3)=[O:14])[O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)=[O:52])([CH3:65])([CH3:64])[CH3:63]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 178522097HCID 178522097, compound

Product 1

HCID 178452692HCID 178452692, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
60 °C

Procedure

Trans-4-carboxy-3-[4-(2-oxopyrrolidin-1-yl)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (325 mg) obtained in Example 422 is dissolved in t-butanol (8 ml), and thereto are added at room temperature triethylamine (91 μl) and diphenylphosphoryl azide (140 μl), and the mixture is stirred at 60° C. for 1.5 hour, and then heated under reflux for 5.5 hours. The reaction solution is diluted with a saturated aqueous sodium hydrogen carbonate solution, and extracted with chloroform. The organic layer is washed with a saturated brine, dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: chloroform/methanol=100/1, then 10/1) to give the title compound (141.7 mg).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5.5 hours
  3. extractionextracted with chloroform
  4. washThe organic layer is washed with a saturated brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is evaporated under reduced pressure
  7. customThe resulting residue is purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-1a0bbb8bab444ee5938362d3db7438f4
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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