Chlorosulfonic acid → 6-[2-(4-Chlorosulfonyl-3,5-dimethyl-phenoxy)acetylamino]hexanoic acid 2-(3-nitro-benzenesulfonyl)ethyl ester

HRID 2182852Notes

Reaction equation

HRID 2182852 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([CH2:13][CH2:14][O:15][C:16](=[O:35])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:34])[CH2:24][O:25][C:26]2[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[CH:27]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Cl:36][S:37](O)(=[O:39])=[O:38]>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([CH2:13][CH2:14][O:15][C:16](=[O:35])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:34])[CH2:24][O:25][C:26]2[CH:31]=[C:30]([CH3:32])[C:29]([S:37]([Cl:36])(=[O:39])=[O:38])=[C:28]([CH3:33])[CH:27]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 695572376-[2-(3,5-Dimethyl-phenoxy)acetylamino]hexanoic Acid 2-(3-nitrobenzenesulfonyl)ethyl Ester2×

Product 1

HCID 878889196-[2-(4-Chlorosulfonyl-3,5-dimethyl-phenoxy)acetylamino]hexanoic acid 2-(3-nitro-benzenesulfonyl)ethyl esterYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of 6-[2-(3,5-dimethyl-phenoxy)acetylamino]hexanoic acid 2-(3-nitrobenzenesulfonyl)ethyl ester (Intermediate 16, 4.6 g, 9.1 mmol) in 3 mL of CH2Cl2 was added drop-wise ClSO3H (3 mL, 5 eq., 45.5 mmol)) at 0° C. During the reaction small aliquots of the reaction mixture were taken out as samples, treated with ice, extracted with ethyl acetate, and the ethyl acetate layers were analyzed by thin layer chromatography (TLC). TLC analysis showed that the reaction was complete after 30 min. Then the resulting thick reaction mixture was poured onto the crushed ice with vigorous stirring to give a yellow gummy material mostly in the bottom of the flask. This mixture was extracted with CH2Cl2, the organic layers were dried over anhydrous MgSO4, and concentrated under reduced pressure to give Intermediate 17 (2.2 g, 40%) as a white foam.

Workup

  1. additiontreated with ice
  2. extractionextracted with ethyl acetate
  3. additionThen the resulting thick reaction mixture was poured onto the crushed ice
  4. customto give a yellow gummy material mostly in the bottom of the flask
  5. extractionThis mixture was extracted with CH2Cl2
  6. dry with materialthe organic layers were dried over anhydrous MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c1cb8c5d075841afad923b814e6f187d
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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