Tetrahydrofuran → HCID 86649392, compound

HRID 1183081Notes

Reaction equation

HRID 1183081 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C1COCC1.[OH:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:28][CH2:29][N:30]1[CH:35]=[CH:34][C:33]2[CH:36]=[CH:37][O:38][C:32]=2[C:31]1=[O:39])[S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-:27])=[O:26])(=[O:18])=[O:17].C(N(CC)CC)C>ClCCl.O>[CH3:1][S:2]([O:11][CH2:12][CH2:13][CH2:14][N:15]([S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-:27])=[O:26])(=[O:17])=[O:18])[CH2:28][CH2:29][N:30]1[CH:35]=[CH:34][C:33]2[CH:36]=[CH:37][O:38][C:32]=2[C:31]1=[O:39])(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68672779HCID 68672779, compound

Product 1

HCID 86649392HCID 86649392, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.14 ml, 1.8 mmol) was added to a THF solution (30 ml) of N-(3-hydroxypropyl)-2-nitro-N-[2-(7-oxo-7H-furo[2,3-c]pyridin-6-yl)ethyl]benzenesulfonamide (644 mg, 1.5 mmol) and triethylamine (0.34 ml, 2.3 mmol), and stirred at room temperature overnight. Water was added to the reaction mixture, and extraction with dichloromethane was performed. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=1:0→10:1). The purified product was concentrated to dryness under reduced pressure to thereby obtain 480 mg (yield: 64%) of 3-{(2-nitrobenzenesulfonyl)-[2-(7-oxo-7H-furo [2,3-c]pyridin-6-yl)ethyl]amino}propyl methanesulfonate as a white amorphous solid.

Workup

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=1:0→10:1)
  4. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-48af23401cbb4588b0d3e2efaae07f88
Source dataset
uspto-grants-2014_03
Patent number
US08664217B2

Reaction notes

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