4-Chlorobenzenesulfonyl chloride → HCID 14986647, compound

HRID 1494087Notes

Reaction equation

HRID 1494087 reaction equation
[H][H].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[C:21]([OH:23])=[O:22])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[CH2:35](N(CC)CC)[CH3:36].ClC1C=CC(S(Cl)(=O)=O)=CC=1.[C:53]([O:56][CH2:57][CH3:58])(=[O:55])C>CO.N.[Ni]>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)([C:53]([O:56][CH2:57][CH3:58])=[O:55])[C:21]([O:23][CH2:35][CH3:36])=[O:22])(=[O:11])=[O:12])=[CH:8][CH:9]=1

Participants

9

Reactant 5

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 9982645HCID 9982645, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14986647HCID 14986647, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

The above compound (4 g) is dissolved in 75 mL of methanol saturated with ammonia gas, activated Raney Nickel is added and the mixture hydrogenated in an atmosphere of hydrogen at 3 atmospheres pressure for 20 hours. The catalyst is filtered off and the methanol solution evaporated to give a residue which is taken up in ethyl acetate. The solution of the resulting amine is treated with 5 mL of triethylamine and 3 g of 4-chlorobenzenesulfonyl chloride. The reaction mixture is evaporated to give a residue which is purified by chromatography over silica gel using a mixture of ether/hexane (7:3) as eluent to yield ethyl 7-(3-pyridyl)-2-ethoxycarbonyl-2-[6-(p-chloro- phenylsulfonamido)-hexyl]-heptanoate, also named ethyl 8-(p-chlorophenylsulfonamido)-2-[5-(3-pyridyl)-pentyl]-2-(ethoxycarbonyl)-octanoate.

Workup

  1. additionis added
  2. filtrationThe catalyst is filtered off
  3. customthe methanol solution evaporated
  4. customto give a residue which
  5. customThe reaction mixture is evaporated
  6. customto give a residue which
  7. customis purified by chromatography over silica gel using
  8. additiona mixture of ether/hexane (7:3) as eluent

Sources & evidence

ORD record
ord-142cc0a56cf24954afc813f415981234
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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