Pyridine, hydrofluoride (1:1) → HCID 86746456, compound

HRID 1645895Notes

Reaction equation

HRID 1645895 reaction equation
[CH3:1][CH:2]([CH2:41][CH3:42])[C:3]([O:5][CH:6]1[CH:15]2[CH:10]([CH2:11][CH2:12][CH:13]([CH3:35])[CH:14]2[CH2:16][CH2:17][CH:18]2[CH2:23][CH:22]([O:24][CH2:25][O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:21][C:20](=[O:34])[O:19]2)[CH2:9][CH:8]([O:36]C(C)(C)C)[CH2:7]1)=[O:4].C1C=CN=CC=1.F>C(#N)C.C(OCC)(=O)C>[CH3:1][CH:2]([CH2:41][CH3:42])[C:3]([O:5][CH:6]1[CH:15]2[CH:10]([CH2:11][CH2:12][CH:13]([CH3:35])[CH:14]2[CH2:16][CH2:17][CH:18]2[CH2:23][CH:22]([O:24][CH2:25][O:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:21][C:20](=[O:34])[O:19]2)[CH2:9][CH:8]([OH:36])[CH2:7]1)=[O:4]

Participants

5

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 86746455HCID 86746455, compound

Product 1

HCID 86746456HCID 86746456, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 28.8 g (44.7 mmol) of intermediate 3B in 400 ml of acetonitrile was cooled at -20° C. under argon and treated with three 10 ml portions of HF-pyridine over 2 hours, with warming to 0° C. after 1.5 hours. The reaction mixture was diluted with 500 ml of ethyl acetate and washed sequentially with saturated copper sulfate (aqueous 2×150 ml), brine (1×250, 200 and 150 ml) and saturated sodium bicarbonate (aqueous, 2×250 ml, 1×200 ml). After drying the ethyl acetate solution with sodium sulfate and concentrating, the crude product was purified by silica gel chromatography, eluting with 40% hexanes in ethyl acetate to yield 2.2 g (93.7%) of intermediate 3C as a clear, colorless oil.

Workup

  1. washwashed sequentially with saturated copper sulfate (aqueous 2×150 ml), brine (1×250, 200 and 150 ml) and saturated sodium bicarbonate (aqueous, 2×250 ml, 1×200 ml)
  2. dry with materialAfter drying the ethyl acetate solution with sodium sulfate
  3. concentrationconcentrating
  4. customthe crude product was purified by silica gel chromatography
  5. washeluting with 40% hexanes in ethyl acetate

Sources & evidence

ORD record
ord-4277374c45714671b80f268a52a9e35a
Source dataset
uspto-grants-1993_01
Patent number
US05177104

Reaction notes

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