Triethylamine → HCID 59750849, compound

HRID 748771Notes

Reaction equation

HRID 748771 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4]C)C.C1C=CC([O:14]P(OC2C=CC=CC=2)(N=[N+]=[N-])=O)=CC=1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([S:34]([CH:37]([C:44]2[CH:49]=[C:48]([F:50])[CH:47]=[CH:46][C:45]=2[F:51])[CH2:38]CCC(O)=O)(=[O:36])=[O:35])=[CH:30][CH:29]=1.[I:52][CH2:53][CH2:54][OH:55]>C(OCC)(=O)C.C(OCC)(=O)C.CCCCCC.CCCCCC.C1(C)C=CC=CC=1>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([S:34]([CH:37]([C:44]2[CH:49]=[C:48]([F:50])[CH:47]=[CH:46][C:45]=2[F:51])[CH2:38][CH2:7][CH2:6][NH:3][C:4](=[O:14])[O:55][CH2:54][CH2:53][I:52])(=[O:36])=[O:35])=[CH:30][CH:29]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 12225IodoethanolHCID 123414Diphenylphosphoryl azideHCID 59750943HCID 59750943, compound

Product 1

HCID 59750849HCID 59750849, compoundYield 52.2%

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Under a nitrogen atmosphere and at 0° C., triethylamine (157 μl, 1.13 mmol) and diphenylphosphoric azide (243 μl, 1.13 mmol) were added to a toluene solution (5 ml) of the 5-[(4-chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)valeric acid (400 mg, 1.03 mmol) obtained in Example 202. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was heated under reflux for 3 hours. After cooling to room temperature and addition of 2-iodoethanol (160 μl, 2.06 mmol), the mixture was heated under reflux for further 1.5 hours. The reaction mixture diluted with ethyl acetate was then washed successively with a saturated aqueous solution of sodium bicarbonate, water, and brine, dried over magnesium sulfate and then, concentrated. The residue thus obtained was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=3:1 eluate was concentrated. The solid thus obtained was recrystallized from ethyl acetate-hexane, whereby the title compound (300 mg, 0.538 mmol, 52%) was obtained as colorless needle crystals.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling to room temperature
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for further 1.5 hours
  6. washwas then washed successively with a saturated aqueous solution of sodium bicarbonate, water, and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue thus obtained
  10. concentrationethyl acetate=3:1 eluate was concentrated
  11. customThe solid thus obtained

Sources & evidence

ORD record
ord-73ee4ec454d84c7a916cf9f73d2cb3a1
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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