4-Nitrobenzenesulfonyl chloride → ethyl 2-{[(4-nitrophenyl)sulfonyl]amino}-4-(tetrahydro-4H-pyran-4-ylidene)butanoate

HRID 535146Notes

Reaction equation

HRID 535146 reaction equation
[NH2:1][CH:2]([CH2:8][CH:9]=[C:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].CCN(C(C)C)C(C)C.[N+:25]([C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1)([O-:27])=[O:26]>ClCCl>[N+:25]([C:28]1[CH:29]=[CH:30][C:31]([S:34]([NH:1][CH:2]([CH2:8][CH:9]=[C:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])(=[O:36])=[O:35])=[CH:32][CH:33]=1)([O-:27])=[O:26]

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58313060ethyl 2-amino-4-(tetrahydro-4H-pyran-4-ylidene)butanoate

Product 1

HCID 58313106ethyl 2-{[(4-nitrophenyl)sulfonyl]amino}-4-(tetrahydro-4H-pyran-4-ylidene)butanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 2-amino-4-(tetrahydro-4H-pyran-4-ylidene)butanoate (163) (1.0 g, 4.7 mmol) in anhydrous dichloromethane (30 mL) was added Hunig's base (1.6 mL, 9.4 mmol) followed by 4-nitrobenzenesulfonyl chloride (1.14 g, 5.2 mmol) and the reaction stirred at room temperature under nitrogen for 2 h. The reaction was diluted with dichloromethane and washed with 0.1 N HCl, the organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 10-70% hexanes/EtOAc to afford the title compound as an off-white solid in quantitative yield.

Workup

  1. washwashed with 0.1 N HCl
  2. dry with materialthe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 10-70% hexanes/EtOAc

Sources & evidence

ORD record
ord-f37fb00e5cbc48e58bd70642978897f2
Source dataset
uspto-grants-2014_10
Patent number
US08853416B2

Reaction notes

Loading…