Cesium carbonate → HCID 60010319, compound

HRID 1072077Notes

Reaction equation

HRID 1072077 reaction equation
Cl[CH2:2][C@@H:3]([OH:21])[CH2:4][NH:5][CH2:6][CH2:7][NH:8][S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19])(=[O:11])=[O:10].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[N+:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[S:9]([N:8]1[CH2:2][C@@H:3]([OH:21])[CH2:4][NH:5][CH2:6][CH2:7]1)(=[O:11])=[O:10])([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 67411716HCID 67411716, compound

Product 1

HCID 60010319HCID 60010319, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of N-[2-({2S}-3-chloro-2-hydroxy-propylamino)-ethyl]-2-nitro-benzenesulfonamide (20.73 gm, 61.4 mmole) and Cs2CO3 (73 gm, 3 equiv) in dry acetonitrile (600 mL) under a N2 atmosphere was heated at 60° C. for 6.5 hr. The solid was removed by filtration and then the solvent was removed from the filtrate. The residue was partitioned between DCM (400 mL) and water (100 mL). The organic phase was dried (Na2SO4) and the solvent was removed. Silica gel chromatography (step gradient elution with DCM containing: 0, 1, 2, 3, 4% MeOH) afforded the title compound as an oil (5.68 gm, 31%). 1H NMR (CDCl3+D2O) δ 2.3 (br. s, 2H), 2,85 (m, 4H), 3.09 (m, 4H), 7.68 (m, 3H), 8.00 (m, 1H); MS: 302 (M+H+); HPLC Ret Time: 0.56 min (YMC Xterra 3.0×50 mm S7 C18 column, 3 min gradient, 4 mL/min).

Workup

  1. customThe solid was removed by filtration
  2. customthe solvent was removed from the filtrate
  3. customThe residue was partitioned between DCM (400 mL) and water (100 mL)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customthe solvent was removed
  6. washSilica gel chromatography (step gradient elution with DCM containing: 0, 1, 2, 3, 4% MeOH)

Sources & evidence

ORD record
ord-03f9915a2fce47df960bb4a9dcfcb582
Source dataset
uspto-grants-2005_06
Patent number
US06908916B2

Reaction notes

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