Triethylamine → HCID 86658316, compound

HRID 1966647Notes

Reaction equation

HRID 1966647 reaction equation
[F:1][C:2]([C:13]1[CH:14]=[C:15]([N:19]2[C:23](=[O:24])[CH2:22][NH:21][C:20]2=[O:25])[CH:16]=[CH:17][CH:18]=1)([F:12])[CH2:3][O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35].O.[OH-].[NH4+]>C(Cl)Cl>[CH3:33][S:34]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][O:4][CH2:3][C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N:19]2[C:23](=[O:24])[CH2:22][NH:21][C:20]2=[O:25])[CH:14]=1)([F:1])[F:12])(=[O:36])=[O:35]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67245686HCID 67245686, compoundHCID 86589665Water ammonium hydroxide

Product 1

HCID 86658316HCID 86658316, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Intermediate 62 (1.94 g, 5.45 mmol) was disolved in methylene chloride (15 mL) and triethylamine (1.21 mL, 8.72 mmol) was then added. The mixture was cooled to 0° C. and a solution of methanesulfonyl chloride (0.680 mL, 8.72 mmol) in methylene chloride (5 mL) was slowly added at the same temperature. The mixture was stirred at room temperature for 16 hours. The crude reaction was cooled to 0° C. and then 50% solution water/ammonium hydroxide (40 mL) was added. The organic layer was washed with water (2×40 mL), brine (1×40 mL), dried (Na2SO4) and concentrated. The title compound was obtained (2.4 g, 100%) as oil.

Workup

  1. customThe crude reaction
  2. temperaturewas cooled to 0° C.
  3. washThe organic layer was washed with water (2×40 mL), brine (1×40 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8e3eccba0eba48998ec241302b62ad42
Source dataset
uspto-grants-2013_04
Patent number
US08420669B2

Reaction notes

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