tert-Butanol → HCID 58734256, compound

HRID 2080481Notes

Reaction equation

HRID 2080481 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C([N:20]([CH2:23]C)CC)C.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([CH:35]([C:46]2[CH:51]=[C:50]([F:52])[CH:49]=[CH:48][C:47]=2[F:53])[C:36]2[C:41]([CH3:42])=[CH:40][N:39]=[C:38](C(O)=O)[CH:37]=2)(=[O:34])=[O:33])=[CH:28][CH:27]=1.C(OCC)(=[O:56])C.[C:60]([OH:64])([CH3:63])([CH3:62])[CH3:61]>C1(C)C=CC=CC=1>[C:60]([O:64][C:23](=[O:56])[NH:20][C:38]1[CH:37]=[C:36]([CH:35]([S:32]([C:29]2[CH:28]=[CH:27][C:26]([Cl:25])=[CH:31][CH:30]=2)(=[O:34])=[O:33])[C:46]2[CH:51]=[C:50]([F:52])[CH:49]=[CH:48][C:47]=2[F:53])[C:41]([CH3:42])=[CH:40][N:39]=1)([CH3:63])([CH3:62])[CH3:61]

Participants

7

Reactant 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 23114575HCID 23114575, compound

Product 1

HCID 58734256HCID 58734256, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, diphenylphosphoryl azide (2.9 ml, 13.6 mmol) and triethylamine (2.7 ml, 19.4 mmol) were added to a solution of 4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]-5-methylpicolinic acid (2.8 mg, 6.40 mmol) in a mixture of t-butanol (20 ml) and toluene (40 ml). The resulting mixture was stirred for 16 hours under heating and refluxing. After cooling, ethyl acetate was added to the reaction mixture. The resulting mixture was washed sequentially with a saturated aqueous solution of sodium bicarbonate and brine. The organic layer thus obtained was dried over magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was washed sequentially with hexane and ethyl acetate to give the title compound (2.60 g, 5.11 mmol, 80%) as a white powder.

Workup

  1. temperatureunder heating
  2. temperaturerefluxing
  3. temperatureAfter cooling
  4. washThe resulting mixture was washed sequentially with a saturated aqueous solution of sodium bicarbonate and brine
  5. customThe organic layer thus obtained
  6. dry with materialwas dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus obtained
  9. washwas washed sequentially with hexane and ethyl acetate

Sources & evidence

ORD record
ord-d514787682744336b64228a1e46c6af1
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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