Triethylamine → HCID 86617446, compound

HRID 2353015Notes

Reaction equation

HRID 2353015 reaction equation
[F:1][C:2]([F:26])([C:22]([F:25])([F:24])[F:23])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21].CCN(CC)CC.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[F:1][C:2]([F:26])([C:22]([F:23])([F:24])[F:25])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][S:35]([CH3:34])(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59649298HCID 59649298, compound

Product 1

HCID 86617446HCID 86617446, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a clean flame dried 250 mL RBF under current of N2, was added 10.10 g (26 mmol) of 55. To this was added 100 mL of DCM and 5.5 mL (39 mmol) of Et3N. The reaction mixture was then cooled in an ice-water bath and 2.3 mL (29 mmol) of MsCl was added and stirred for 12 h at room temperature. The reaction was then diluted with 200 mL of DCM and washed successively with sat. aq. NaHCO3 (1×), H2O (2×), brine (1×), dried over MgSO4, filtered and the solvent evaporated under vacuum. The residue was then purified using combiflash (120 g silica column) with hexane/ethyl acetate as eluent to furnish 10.15 g (84%) of target product 56 as a white solid.

Workup

  1. temperatureInto a clean flame
  2. dry with materialdried 250 mL RBF under current of N2
  3. temperatureThe reaction mixture was then cooled in an ice-water bath
  4. washwashed successively with sat. aq. NaHCO3 (1×), H2O (2×), brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent evaporated under vacuum
  8. customThe residue was then purified

Sources & evidence

ORD record
ord-72764a73149444d6b9d7e8f7216e6e27
Source dataset
uspto-grants-2010_07
Patent number
US07749983B2

Reaction notes

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