Triethylamine → HCID 87560978, compound

HRID 885128Notes

Reaction equation

HRID 885128 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:20][CH2:21][CH2:22][OH:23])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl-].[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38]([O-])(=[O:40])=[O:39])=[CH:34][CH:33]=1>CN(C)C1C=CN=CC=1.ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([O:20][CH2:21][CH2:22][O:23][S:38]([C:35]3[CH:36]=[CH:37][C:32]([CH3:42])=[CH:33][CH:34]=3)(=[O:40])=[O:39])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[CH2:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 22024621p-Toluenesulfonate chlorideHCID 68750433HCID 68750433, compound

Product 1

HCID 87560978HCID 87560978, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To an ambient solution of Example 54C (0.450 g, 1.17 mmol), triethylamine (0.178 mL, 1.28 mmol), and 4-dimethylaminopyridine (0.005 g, 0.041 mmol) in dichloromethane (3 mL) was added p-toluenesulfonate chloride (0.224 g, 1.17 mmol). The reaction was stirred at room temperature for 8 h and was then partitioned between water (10 mL) and dimethyl ether (10 mL). The layers were separated, and the aqueous was extracted with additional diethyl ether (2×10 mL). The combined organic layers were dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by MPLC (10% ethyl acetate in hexane to 25% ethyl acetate in hexane) to give the title product. MS (ESI) m/z 541[M+H]+.

Workup

  1. customwas then partitioned between water (10 mL) and dimethyl ether (10 mL)
  2. customThe layers were separated
  3. extractionthe aqueous was extracted with additional diethyl ether (2×10 mL)
  4. dry with materialThe combined organic layers were dried with anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by MPLC (10% ethyl acetate in hexane to 25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f8e5e4b3accf40209b40b1e389d01c00
Source dataset
uspto-grants-2012_08
Patent number
US08242139B2

Reaction notes

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