Perfluoro-1-butanesulfonyl fluoride → Perfluoro-1-butanesulfonic acid 7-methoxy-1-[4-((R)-1-phenyl-ethoxy)-phthalazin-1-yl)-naphthalen-2-yl ester

HRID 1711981

Reaction equation

HRID 1711981 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([OH:32])=[C:10]2[C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23][C@@H:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:25])=[N:15][N:14]=2)=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[F:42][C:43]([F:58])([S:54](F)(=[O:56])=[O:55])[C:44]([F:53])([F:52])[C:45]([F:51])([F:50])[C:46]([F:49])([F:48])[F:47]>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([O:32][S:54]([C:43]([F:42])([F:58])[C:44]([F:52])([F:53])[C:45]([F:50])([F:51])[C:46]([F:49])([F:48])[F:47])(=[O:56])=[O:55])=[C:10]2[C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23][C@@H:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:25])=[N:15][N:14]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 81531DiisopropylethylamineHCID 1363525037-Methoxy-1-[4-((R)-1-phenyl-ethoxy)-phthalazin-1-yl]-naphthalen-2-ol

Product 1

HCID 86602155Perfluoro-1-butanesulfonic acid 7-methoxy-1-[4-((R)-1-phenyl-ethoxy)-phthalazin-1-yl)-naphthalen-2-yl esterYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 7-methoxy-1-[4-((R)-1-phenyl-ethoxy)-phthalazin-1-yl]-naphthalen-2-ol (1.0 g, 2.4 mmol) in diisopropylethylamine (0.94 ml, 7.1 mmol) and dichloromethane (35 ml) was treated with N,N-dimethylaminopyridine (DMAP, 50 mg, 0.41 mmol) at 0° C. Then perfluoro-1-butanesulfonyl fluoride (0.51 ml, 2.8 mmol) was added dropwise and the resulting solution was stirred for 19 hrs at 23° C. The resulting solution was quenched with sat. aqueous ammonium chloride solution. The organic layer was separated and the water layer was extracted twice with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (hexane/EtOAc 3:1) to give 1.4 g (2.0 mmol) of the title compound as an oil.

Workup

  1. customThe resulting solution was quenched with sat. aqueous ammonium chloride solution
  2. customThe organic layer was separated
  3. extractionthe water layer was extracted twice with dichloromethane
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (hexane/EtOAc 3:1)

Sources & evidence

ORD record
ord-7d724ff8c31f48fe9d5c48914b96e1c2
Source dataset
uspto-grants-2010_09
Patent number
US07790882B2

Linked notes

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