Tetrahydrofuran → HCID 86649392, compound

HRID 2196065Notes

Reaction equation

HRID 2196065 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→0:1). 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→0:1)
  4. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1129b0a2261f43db86f5b896c6969744
Source dataset
uspto-grants-2012_12
Patent number
US08338406B2

Reaction notes

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