Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 19759865, compound

HRID 1586870Notes

Reaction equation

HRID 1586870 reaction equation
[CH2:1]([C:4]1([C:14]([OH:16])=O)[S:11](=[O:13])(=[O:12])[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH2:5]1)[CH:2]=[CH2:3].CN([P+](O[N:28]1N=N[C:30]2C=CC=C[C:29]1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:29]([NH:28][C:14]([C:4]1([CH2:1][CH:2]=[CH2:3])[S:11](=[O:12])(=[O:13])[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH2:5]1)=[O:16])[CH3:30]

Participants

4

Reactant 2

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 19759863HCID 19759863, compound

Product 1

HCID 19759865HCID 19759865, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-allyl-2,3-dihydrothieno[2,3-b]thiophene-2-carboxylic acid-1,1-dioxide (8 g, 0.031 mol) and BOP reagent (17.8 g, 0.041 mol) in degassed DMF (150 mL) was cooled to 0° C. under nitrogen. Ethylamine was bubbled into the stirred reaction mixture until the solution was quite basic. After 1.5 hours, the DMF was removed in vacuo and the residue partitioned between ethyl acetate and 6N HCl. The aqueous phase was extracted a total of four times with ethyl acetate and the combined extracts washed with saturated sodium bicarbonate, brine, then dried over magnesium sulfate. Filtration and solvent removal gave the title compound as an oil (7.2 g).

Workup

  1. customEthylamine was bubbled into the stirred reaction mixture until the solution
  2. customthe DMF was removed in vacuo
  3. customthe residue partitioned between ethyl acetate and 6N HCl
  4. extractionThe aqueous phase was extracted a total of four times with ethyl acetate
  5. washthe combined extracts washed with saturated sodium bicarbonate, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationFiltration and solvent removal

Sources & evidence

ORD record
ord-83e1d2b8ad474efdb0190c804141f100
Source dataset
uspto-grants-1993_06
Patent number
US05216020

Reaction notes

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