Diisopropylethylamine → HCID 89933234, compound

HRID 1500944Notes

Reaction equation

HRID 1500944 reaction equation
Cl.[O:2]=[S:3]1(=[O:9])[CH2:7][CH2:6][C@@H:5]([NH2:8])[CH2:4]1.CCN(C(C)C)C(C)C.FC(F)(F)S(O[C:25]1[C:30]([N+:31]([O-:33])=[O:32])=[CH:29][C:28]([Cl:34])=[CH:27][C:26]=1[F:35])(=O)=O>C1COCC1.O>[Cl:34][C:28]1[CH:29]=[C:30]([N+:31]([O-:33])=[O:32])[C:25]([NH:8][C@@H:5]2[CH2:6][CH2:7][S:3](=[O:9])(=[O:2])[CH2:4]2)=[C:26]([F:35])[CH:27]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 670412613-Thiophenamine, tetrahydro-, 1,1-dioxide, hydrochloride (1:1), (3R)-HCID 89923571HCID 89923571, compound

Product 1

HCID 89933234HCID 89933234, compoundYield 5.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-1,1-dioxo-tetrahydro-1λ6-thiophen-3-ylamine hydrochloride (9.0 g, 52.43 mmol) in 400 mL of THF was added DIPEA (27.0 g, 210 mmol), followed by addition of a solution of 4-chloro-2-fluoro-6-nitrophenyl trifluoromethanesulfonate (20.36 g, 62.92 mmol). After being stirred at RT for 48 hours, the resulting mixture was diluted with water, and then extracted with EtOAc. The organic layer was washed by brine, and then dried over anhydrous Na2SO4, then filtered and concentrated. The residue was purified by flash chromatography to give 0.9 g of (4-chloro-2-fluoro-6-nitrophenyl)-((R)-1,1-dioxo-tetrahydro-1λ6-thiophen-3-yl)-amine.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed by brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b9c8353f6f9e4d47908a333e3ddb2b8c
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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