4-Nitrobenzenesulfonyl chloride → HCID 57026850, compound

HRID 1815556Notes

Reaction equation

HRID 1815556 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][C:7](S(Cl)(=O)=O)=[CH:6][CH:5]=1)([O-])=O.[CH2:14]([N:16](C(C)C)C(C)C)C.[OH:23][C@H:24]([CH2:49]NCC(C)C)[C@@H:25]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34]C2C=CC=CN=2)=[CH:29][CH:28]=1>ClCCl>[C:14]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:4]=1)[CH2:34][O:33][C:30]1[CH:29]=[CH:28][C:27]([CH2:26][C@H:25]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:45])([CH3:46])[CH3:47])[C@H:24]2[CH2:49][O:23]2)=[CH:32][CH:31]=1)#[N:16]

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 59997314HCID 59997314, compound

Product 1

HCID 57026850HCID 57026850, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the product from the previous step (0.42 g, 0.96 mmol) in 20 mL of anhydrous dichloromethane were added 4-nitrobenzenesulfonyl chloride (0.25 g, 1.1 mmol) and N-ethyldiisopropylamine (0.15 g, 1.7 mmol). The mixture was allowed to react for the given number of hours [1] and at which time the solvent was removed under reduced pressure. The residue was redissolved in dichlormethane and extracted with water (3×50 mL). The organic phase was dried with magnesium sulfate, filtered, and removed under reduced pressure. The residue was purified on silica gel using ethyl acetate-hexanes [2] as eluent to provide the following compounds [Y:(3)]:

Workup

  1. customwas removed under reduced pressure
  2. dissolutionThe residue was redissolved in dichlormethane
  3. extractionextracted with water (3×50 mL)
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. filtrationfiltered
  6. customremoved under reduced pressure
  7. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-691683dddde8437db6c22ff029a631a2
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

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