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

HRID 2182855Notes

Reaction equation

HRID 2182855 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([CH2:13][CH2:14][O:15][C:16](=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:32])[CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Cl:34][S:35](O)(=[O:37])=[O:36]>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([CH2:13][CH2:14][O:15][C:16](=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:32])[CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([S:35]([Cl:34])(=[O:37])=[O:36])=[CH:28][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 695572526-(2-Phenoxy-acetylamino)-n-hexanoic acid 2-(3-nitrobenzenesulfonyl)ethyl ester

Product 1

HCID 865925656-[2-(4-Chlorosulfonyl-phenoxy)-acetylamino]-n-hexanoic acid 2-(3-nitro-benzenesulfonyl)ethyl esterYield 60.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of 6-(2-phenoxy-acetylamino)-n-hexanoic acid 2-(3-nitro-benzenesulfonyl)ethyl ester (4.5 g, 9.4 mmol) in 10 mL of CH2Cl2 was added drop-wise ClSO3H (3.3 mL, 5.5 g, 5 eq., 47.0 mmol)) at 0° C. The chlorosulfonylation reaction was complete in 30 min. The thick reaction mixture was poured onto the crushed ice with vigorous stirring, resulting in a yellow gummy material mostly in the bottom of the flask. The mixture was extracted with CH2Cl2, the organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a syrupy material, which was purified by column chromatography (CH2Cl2 to 1% MeOH in CH2Cl2) to give 6-[2-(4-chlorosulfonyl-phenoxy)-acetylamino]-n-hexanoic acid 2-(3-nitro-benzenesulfonyl)ethyl ester (Intermediate 19, 3.3 g, 60%) as a white foam.

Workup

  1. customThe chlorosulfonylation reaction
  2. customresulting in a yellow gummy material mostly in the bottom of the flask
  3. extractionThe mixture was extracted with CH2Cl2
  4. dry with materialthe organic layers were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a syrupy material, which
  7. customwas purified by column chromatography (CH2Cl2 to 1% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-e84ca7a78e3f48c0bf501fd45623011c
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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