4-Chlorobenzenesulfonyl chloride → HCID 11742328, compound

HRID 1494083Notes

Reaction equation

HRID 1494083 reaction equation
Cl.[NH2:2][CH2:3][CH:4]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].C(N(CC)CC)C.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>C(OCC)(=O)C>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([NH:2][CH2:3][CH:4]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 19874740HCID 19874740, compound

Product 1

HCID 11742328HCID 11742328, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Methyl 7-amino-6-(3-pyridyl)-heptanoate hydrochloride (8.0 g) is suspended in 200 mL of ethyl acetate, 15 mL of triethylamine is added, and then a solution of 10 g of 4-chlorophenylsulfonyl chloride in 100 mL of ethyl acetate is added dropwise over a period of 0.5 hour. The reaction is then stirred for 2 hours and is extracted with 1N aqueous sodium hydroxide, washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated. The residue is chromatographed over activated magnesium silicate (Florisil) and eluted with ethyl acetate to yield methyl 7-(p-chlorophenylsulfonamido)-6-(3-pyridyl)-heptanoate as an oil.

Workup

  1. extractionis extracted with 1N aqueous sodium hydroxide
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue is chromatographed over activated magnesium silicate (Florisil)
  6. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-c9263d7814e243d5bf4f67f446d06d19
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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