Pentafluorophenol → 2-(S)-(2,2-dimethyl-5-oxo-1.3-dioxolan-4-(R)-yl)-4-methylpentanoic acid pentafluorophenyl ester

HRID 1377630Notes

Reaction equation

HRID 1377630 reaction equation
[CH3:1][C:2]1([CH3:16])[O:6][C@H:5]([C@H:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:8]([OH:10])=[O:9])[C:4](=[O:15])[O:3]1.[F:17][C:18]1[C:23](O)=[C:22]([F:25])[C:21]([F:26])=[C:20]([F:27])[C:19]=1[F:28]>C(Cl)Cl>[F:17][C:18]1[C:23]([O:9][C:8](=[O:10])[C@H:7]([C@@H:5]2[C:4](=[O:15])[O:3][C:2]([CH3:1])([CH3:16])[O:6]2)[CH2:11][CH:12]([CH3:13])[CH3:14])=[C:22]([F:25])[C:21]([F:26])=[C:20]([F:27])[C:19]=1[F:28]

Participants

4

Reactant 2

HCID 13041PentafluorophenolHCID 22876674HCID 22876674, compound

Product 1

HCID 537488672-(S)-(2,2-dimethyl-5-oxo-1.3-dioxolan-4-(R)-yl)-4-methylpentanoic acid pentafluorophenyl esterYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(S)-(2,2-dimethyl-5-oxo-1.3-dioxolan-4-(R)-yl)-4-methylpentanoic acid (1.1 g, 4.78 mmole), pentafluorophenol (970 mg, 5.27 mmole), and 1-dimethylaminopropyl-3-ethyl carbodiimide methiodide (1.42 g, 4.78 mmole) in CH2Cl2 (25 ml) was stirred at 23° for 24 h. The reaction was washed with H2O, 5% aqueous K2CO3, H2O, dried (K2CO3), and the solvent evaporated, to yield the title compound (1.39 g, 74%).

Workup

  1. washThe reaction was washed with H2O, 5% aqueous K2CO3, H2O
  2. dry with materialdried (K2CO3)
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-79244a793e4d4166817bdf24888ef764
Source dataset
uspto-grants-1997_09
Patent number
US05665753

Reaction notes

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