Potassium Carbonate → HCID 117697843, compound

HRID 1778526Notes

Reaction equation

HRID 1778526 reaction equation
[CH:1]12[NH:9][CH:5]([C:6](=[O:8])[CH2:7]1)[CH2:4][O:3][CH2:2]2.C([O-])([O-])=O.[K+].[K+].[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](Cl)(=[O:27])=[O:26])([O-:18])=[O:17]>CC#N>[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([N:9]1[CH:5]2[C:6](=[O:8])[CH2:7][CH:1]1[CH2:2][O:3][CH2:4]2)(=[O:27])=[O:26])([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 155402-Nitrobenzenesulfonyl chlorideHCID 117697855HCID 117697855, compound

Product 1

HCID 117697843HCID 117697843, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of compound 108b (100 mg), TEA (102 mg), K2CO3 (207 mg, 1.5 mmol, 3.0 eq) and 2-nitro-benzenesulfonyl chloride (222 mg) in MeCN (10 mL) was stirred at room temperature for 10 h. Then the solvent was removed in vacuo, the residue was purified by silica gel (EA/PE=1:3) to give 8-(2-nitrophenyl)sulfonyl-3-oxa-8-azabicyclo[3.2.1]octan-6-one 108c as a white solid, 100 mg. MS: calc'd (MH+) 313, measured (MH+) 313.

Workup

  1. customThen the solvent was removed in vacuo
  2. customthe residue was purified by silica gel (EA/PE=1:3)

Sources & evidence

ORD record
ord-7466af5ff1474dd5b7703d11c9129f2d
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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