Hexane → HCID 59750780, compound

HRID 748782Notes

Reaction equation

HRID 748782 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([OH:33])[CH:14]([S:23]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24])[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[F:22])(C(C)(C)C)(C)C.N1C=CC=CC=1.F.CCCCCC.C(OCC)(=O)C.CCCCCC>O1CCCC1.C(OCC)(=O)C>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([S:23]([CH:14]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])[CH:13]([OH:33])[CH2:12][CH2:11][CH2:10][CH2:9][OH:8])(=[O:25])=[O:24])=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 64774Pyridine, hydrofluoride (1:1)HCID 21226206Ethyl acetate hexaneHCID 597508896-(t-Butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]-1-(2,5-difluorophenyl)-2-hexanol

Product 1

HCID 59750780HCID 59750780, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 6-(t-butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]-1-(2,5-difluorophenyl)-2-hexanol (Isomer 234-B) (120 mg, 0.231 mmol) obtained in Example 234 was dissolved in tetrahydrofuran (5 ml), followed by the addition of hydrogen fluoride-pyridine (0.5 ml). The resulting mixture was stirred at room temperature for 20 hours. The reaction mixture was diluted with ethyl acetate, washed successively with water, a saturated aqueous solution of sodium bicarbonate, and brine, dried over magnesium sulfate and then, concentrated. The residue thus obtained was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=1:1 eluate was concentrated. The solid thus obtained was recrystallized from ethyl acetate-hexane, whereby the title compound (51.3 mg, 0.127 mmol, 55%) was obtained as a white powder.

Workup

  1. washwashed successively with water
  2. dry with materiala saturated aqueous solution of sodium bicarbonate, and brine, dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue thus obtained
  5. concentrationethyl acetate=1:1 eluate was concentrated
  6. customThe solid thus obtained

Sources & evidence

ORD record
ord-029426189b8041e2bfecaeaee04d26ce
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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