(Diethylamino)sulfur trifluoride → HCID 86692272, compound

HRID 1469798Notes

Reaction equation

HRID 1469798 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:13])[C:5]([CH2:14][NH:15][C:16](=[O:22])[C:17]([CH3:21])([CH3:20])[CH2:18]O)=[CH:4][CH:3]=1.C(N(S(F)(F)[F:29])CC)C>C1COCC1>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:13])[C:5]([CH2:14][NH:15][C:16](=[O:22])[C:17]([CH3:21])([CH3:20])[CH2:18][F:29])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 86692262HCID 86692262, compound

Product 1

HCID 86692272HCID 86692272, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 6-chloro-2-fluoro-3-((3-hydroxy-2,2-dimethylpropanamido)methyl)benzoate (Intermediate-59, step 1, 200 mg, 0.60 mmol) in THF (2 mL) was added diethylaminosulfur trifluoride (146 mg, 0.90 mmol) and the reaction mixture was stirred at rt for 12 h. Then the reaction mixture was quenched with water and was extracted with CHCl3. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 0.104 g of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.32 (t, 1H), 7.44-7.36 (m, 2H), 4.47-4.29 (m, 6H), 1.33-1.29 (t, J=6.9 Hz, 3H), 1.14 (s, 6H).

Workup

  1. customThen the reaction mixture was quenched with water
  2. extractionwas extracted with CHCl3
  3. washThe organic layer was washed with brine
  4. customseparated
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-60c4ae4065d7497d9cfb4880775125e3
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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