Water → HCID 59750737, compound

HRID 748772Notes

Reaction equation

HRID 748772 reaction equation
[H-].[Na+].O1CCCC1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH:18]([C:29]2[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=2[F:36])[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:28])[O:24][CH2:25][CH2:26]I)(=[O:17])=[O:16])=[CH:11][CH:10]=1.O>C(OCC)(=O)C.CCCCCC.CCCCCC>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH:18]([C:29]2[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=2[F:36])[CH2:19][CH2:20][CH2:21][N:22]2[CH2:26][CH2:25][O:24][C:23]2=[O:28])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 59750849HCID 59750849, compound

Product 1

HCID 59750737HCID 59750737, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Under a nitrogen atmosphere and at 0° C., sodium hydride (60% dispersion in mineral oil, 13.6 mg, 0.340 mmol) was added to a tetrahydrofuran solution (5 ml) of 2-iodoethyl N-[4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)butyl]carbamate (158 mg, 0.283 mmol). The resulting mixture was stirred at room temperature for 18 hours. Water was added to the reaction mixture, followed by extraction wth ethyl acetate. The extract was washed with 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=1:2 eluate was concentrated. The solid thus obtained was recrystallized from ethyl acetate-hexane, whereby the title compound (52.1 mg, 0.121 mmol, 43%) was obtained as colorless needle crystals.

Workup

  1. extractionfollowed by extraction wth ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue thus obtained
  6. concentrationethyl acetate=1:2 eluate was concentrated
  7. customThe solid thus obtained

Sources & evidence

ORD record
ord-2cec4a41a43540a591c813dd2dfb092b
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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