Methyl iodide → HCID 59753624, compound

HRID 1693392Notes

Reaction equation

HRID 1693392 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-:26])=[O:25])(=[O:17])=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:27](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([CH3:27])[S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-:26])=[O:25])(=[O:17])=[O:16])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 53255592HCID 53255592, compound

Product 1

HCID 59753624HCID 59753624, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2-nitrobenzenesulfonylamino)piperidine-1-carboxylic acid tert-butyl ester (Preparation 73) (400 mg, 1.04 mmol) in DMF (10 mL) was added caesium carbonate (507 mg, 1.56 mmol) and the mixture stirred at rt for 40 min. Iodomethane (323 μL, 5.19 mmol) was added and the mixture stirred for 16 h. Solvent was removed in vacuo and the crude residue partitioned between ethyl acetate (20 mL) and water (20 mL). The organic layer was separated and washed with 1M HCl (2×20 mL), water (20 mL), then brine (2×20 mL) before being dried (MgSO4). The solvent was removed in vacuo to give the title compound as a yellow powder. δH (d6 DMSO): 8.43 (2H, m), 8.01 (2H, m), 4.00-3.89 (3H, m), 2.83-2.67 (5H, m), 1.54-1.43 (2H, m), 1.39 (9H, s), 1.34-1.24 (2H, m).

Workup

  1. stirringthe mixture stirred for 16 h
  2. customSolvent was removed in vacuo
  3. customthe crude residue partitioned between ethyl acetate (20 mL) and water (20 mL)
  4. customThe organic layer was separated
  5. washwashed with 1M HCl (2×20 mL), water (20 mL)
  6. dry with materialbrine (2×20 mL) before being dried (MgSO4)
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-989682c5b97f40fd91f29285a962bd43
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

Loading…