Triethylamine → HCID 86692163, compound

HRID 2201756Notes

Reaction equation

HRID 2201756 reaction equation
[F:1][C:2]([F:17])([C:13]([F:16])([F:15])[F:14])[C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[S:5](F)(=[O:7])=[O:6].CCN(CC)CC.[CH2:25]([CH:32]1[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([OH:41])[CH:39]=2)[C:34](=[O:42])[NH:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl>[F:9][C:4]([F:10])([S:5]([O:41][C:38]1[CH:39]=[C:40]2[C:35](=[CH:36][CH:37]=1)[C:34](=[O:42])[NH:33][CH:32]2[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)(=[O:7])=[O:6])[C:3]([F:12])([F:11])[C:2]([F:17])([F:1])[C:13]([F:16])([F:15])[F:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 71003969HCID 71003969, compound

Product 1

HCID 86692163HCID 86692163, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of nonafluorobutanesulfonyl fluoride (712 mg, 2.36 mmol) and NEt3 (0.49 mL, 3.54 mmol) in 3 mL of dichloromethane was added 3-benzyl-5-hydroxyisoindolin-1-one (example 1.4, 282 mg, 1.18 mmol) in 2 mL of dichloromethane slowly. This reaction mixture was stirred at room temperature for overnight. TLC showed complete conversion, the solvent was evaporated. The residue was purified by flash-chromatography on silica gel with 30-80% ethyl acetate in hexane, 474 mg (77%) of the product was obtained.

Workup

  1. customthe solvent was evaporated
  2. customThe residue was purified by flash-chromatography on silica gel with 30-80% ethyl acetate in hexane

Sources & evidence

ORD record
ord-4afeb4931f6b4d5a84262c9d7c047999
Source dataset
uspto-grants-2016_06
Patent number
US09365512B2

Reaction notes

Loading…