Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 86603830, compound

HRID 2376192Notes

Reaction equation

HRID 2376192 reaction equation
[O:1]=[C:2]([NH:24][O:25]C1CCCCO1)/[CH:3]=[CH:4]/[C:5]1[CH:6]=[CH:7][C:8]([NH:11][C@@H:12]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]2)=[N:9][CH:10]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CCO>[OH:25][NH:24][C:2](=[O:1])/[CH:3]=[CH:4]/[C:5]1[CH:6]=[CH:7][C:8]([NH:11][C@@H:12]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:13]2)=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86603732HCID 86603732, compound

Product 1

HCID 86603830HCID 86603830, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl (3R)-3-[(5-{(1E)-3-oxo-3-[(tetrahydro-2H-pyran-2-yloxy)amino]-1-propen-1-yl}-2-pyridinyl)amino]-1-pyrrolidinecarboxylate (450 mg) and pyridinium p-toluenesulfonate (261 mg) in EtOH (10 ml) was stirred at 55-60° C. for 9 hours. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture of AcOEt and H2O and adjusted to was adjusted to PH10 with aq.K2CO3 solution. The aqueous solution was adjusted to PH6.5 with aq.HCl solution and extracted with AcOEt. The extract was washed with brine and dried over MgSO4. The solvent was evaporated in vacuo and the residue was washed with IPE to give tert-butyl (3R)-3-({5-[(1E)-3-(hydroxyamino)-3-oxo-1-propen-1-yl]-2-pyridinyl}amino)-1-pyrrolidinecarboxylate (118 mg).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in a mixture of AcOEt and H2O
  3. extractionHCl solution and extracted with AcOEt
  4. washThe extract was washed with brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated in vacuo
  7. washthe residue was washed with IPE

Sources & evidence

ORD record
ord-2a48b76749f6450880a840e623bd5fc5
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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