(Diethylamino)sulfur trifluoride → HCID 178464129, compound

HRID 1170438Notes

Reaction equation

HRID 1170438 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[C:10]1(O)[C:18]2[C:13](=[CH:14][C:15]([C:23]([NH2:25])=[O:24])=[CH:16][C:17]=2[C:19]([F:22])([F:21])[F:20])[N:12]([CH2:26][C@H:27]2[CH2:30][C@H:29]([N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])[CH2:28]2)[C:11]1=[O:36].C(=O)(O)[O-].[Na+].C(N(S(F)(F)[F:49])CC)C>>[ClH:2].[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[C:10]1([F:49])[C:18]2[C:13](=[CH:14][C:15]([C:23]([NH2:25])=[O:24])=[CH:16][C:17]=2[C:19]([F:20])([F:21])[F:22])[N:12]([CH2:26][C@H:27]2[CH2:28][C@H:29]([N:31]([CH2:32][CH3:33])[CH2:34][CH3:35])[CH2:30]2)[C:11]1=[O:36]

Participants

4

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium Bicarbonate2×HCID 178464135HCID 178464135, compound

Product 1

HCID 178464129HCID 178464129, compoundYield 85.8%

Procedure

To the compound of Example 1-4 (150.0 mg, 0.26 mmol) was added saturated aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was dissolved in dichloromethane (2.6 mL), and thereto was added diethylaminosulfur trifluoride (207.9 mg, 1.29 mmol) at −78° C., and the mixture was allowed to warm to room temperature and stirred for 24 hours. To the reaction solution was added saturated aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated, and then purified by silica gel column chromatography (chloroform/methanol/ammonia water 20/1/0 to 10/1/0 to 100/10/1), and then by preparative liquid chromatography. To the purified substance were added tetrahydrofuran and 1M hydrochloric acid (0.5 mL), and the mixture was concentrated. The resulting solid was suspended in diethyl ether and filtered to give the titled compound (65.0 mg, 43%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in dichloromethane (2.6 mL)
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by silica gel column chromatography (chloroform/methanol/ammonia water 20/1/0 to 10/1/0 to 100/10/1)
  11. additionTo the purified substance were added tetrahydrofuran and 1M hydrochloric acid (0.5 mL)
  12. concentrationthe mixture was concentrated
  13. filtrationfiltered

Sources & evidence

ORD record
ord-a070516f26e34a45a2748b24b5d13176
Source dataset
uspto-grants-2010_11
Patent number
US07825155B2

Reaction notes

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