Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 76072303, compound

HRID 2200087Notes

Reaction equation

HRID 2200087 reaction equation
Cl.[F:2][C:3]([F:19])([F:18])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][O:13][CH:12]([CH2:16][NH2:17])[CH2:11]2)=[CH:6][CH:5]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([N:30]([CH:35]([CH3:37])[CH3:36])[CH2:31][C:32](O)=[O:33])(=[O:29])=[O:28])=[CH:23][CH:22]=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>ClCCl>[F:20][C:21]1[CH:22]=[CH:23][C:24]([S:27]([N:30]([CH:35]([CH3:37])[CH3:36])[CH2:31][C:32]([NH:17][CH2:16][CH:12]2[O:13][CH2:14][CH2:15][N:10]([C:7]3[CH:6]=[CH:5][C:4]([C:3]([F:2])([F:18])[F:19])=[CH:9][CH:8]=3)[CH2:11]2)=[O:33])(=[O:28])=[O:29])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 60827977HCID 60827977, compoundHCID 90158386HCID 90158386, compound

Product 1

HCID 76072303HCID 76072303, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-(4-(Trifluoromethyl)phenyl)morpholin-2-yl)methylamine hydrochloride (99 mg, 0.34 mmol), 2-[(4-fluoro-benzenesulfonyl)-isopropyl-amino]-acetic acid (96 mg, 0.35 mmol), BOP reagent (154 mg, 0.35 mmol) and TEA (0.2 mL) were combined in 5 mL of dichloromethane. The mixture was stirred overnight and solvents were evaporated. The residue was extracted with ethyl acetate and water. The organic layer was washed with sodium bicarbonate solution and dried. Solvents were evaporated and the residue was purified by ISCO flash column chromatography (11 g silica gel, ethyl acetate in hexanes 0% to 50%) to give the desired compound as a white solid (133 mg, 74%). [MH]+=517.9.

Workup

  1. customsolvents were evaporated
  2. extractionThe residue was extracted with ethyl acetate and water
  3. washThe organic layer was washed with sodium bicarbonate solution
  4. customdried
  5. customSolvents were evaporated
  6. customthe residue was purified by ISCO flash column chromatography (11 g silica gel, ethyl acetate in hexanes 0% to 50%)

Sources & evidence

ORD record
ord-24229d821ab64a0cb42e7dc15c7089fe
Source dataset
uspto-grants-2016_06
Patent number
US09359337B2

Reaction notes

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