Triethylamine → HCID 68645847, compound

HRID 1160079Notes

Reaction equation

HRID 1160079 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].CCN(CC)CC.Cl.[NH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[C:24]2[B:25]([OH:32])[O:26][CH:27]([CH2:28][N+:29]([O-:31])=[O:30])[C:23]=2[CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[OH:32][B:25]1[C:24]2[C:19]([O:18][CH2:17][CH2:16][CH2:15][NH:14][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:20][CH:21]=[CH:22][C:23]=2[CH:27]([CH2:28][N+:29]([O-:31])=[O:30])[O:26]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68646043HCID 68646043, compound

Product 1

HCID 68645847HCID 68645847, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

MsCl (0.99 mL, 13 mmol) was added slowly to a solution of Et3N (2.85 mL, 20.5 mmol) and 7-(3-amino-propoxy)-3-nitromethyl-3H-benzo[c][1,2]oxaborol-1-ol hydrochloride (1.55 g, 5.12 mmol) in CH2Cl2 (50 mL) at 0° C. (bath temp). The reaction mixture was stirred at rt for 1 h and then quenched with H2O (50 mL). The mixture was extracted with CH2Cl2 and the organic fractions were dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (30% EtOAc in hexane) to give the title compound as a viscous liquid: yield 500 mg (28%).

Workup

  1. customquenched with H2O (50 mL)
  2. extractionThe mixture was extracted with CH2Cl2
  3. dry with materialthe organic fractions were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (30% EtOAc in hexane)

Sources & evidence

ORD record
ord-b47f2e276bf24685bda3f44f12ce35f8
Source dataset
uspto-grants-2010_10
Patent number
US07816344B2

Reaction notes

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