Triethylamine → 3-[N-benzyloxycarbonyl-N-(1-oxido-2-pyridinyl)amino]-propyl methanesulfonate

HRID 2211804Notes

Reaction equation

HRID 2211804 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:19][CH2:20][CH2:21][OH:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N+:13]=1[O-:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>ClCCl>[CH3:30][S:31]([O:22][CH2:21][CH2:20][CH2:19][N:11]([C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N+:13]=1[O-:18])(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 219625733-[N-benzyloxycarbonyl-N-(1-oxido-2-pyridinyl)amino] propanol

Product 1

HCID 219625773-[N-benzyloxycarbonyl-N-(1-oxido-2-pyridinyl)amino]-propyl methanesulfonateYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-[N-benzyloxycarbonyl-N-(1-oxido-2-pyridinyl)-amino] propanol (3 g, 9.92 mmol) and triethylamine (1.2 g, 11.91 mmol) in anhydrous dichloromethane, kept at 0° C. under nitrogen atmosphere, methanesulfonyl chloride (1.36 g, 11.91 mmol) was added, the reaction was allowed to warm to room temperature and stirred for 1 h. The mixture was washed with ice-water, dried with sodium sulfate, filtered and concentrated to give 2.17 g (61%) of 3-[N-benzyloxycarbonyl-N-(1-oxido-2-pyridinyl)amino]-propyl methanesulfonate which, when required, was purified by flash chromatography (dichloromethane/methanol 95:5).

Workup

  1. customkept at 0° C. under nitrogen atmosphere
  2. washThe mixture was washed with ice-water
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9177a67a9cce4a04977728066fd03460
Source dataset
uspto-grants-2006_09
Patent number
US07101876B2

Reaction notes

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