Chlorosulfonic acid → 3-(5-Chlorosulfonyl-2-methoxyphenyl)propionic acid 2-(toluene-4-sulfonyl)ethyl ester

HRID 2182881Notes

Reaction equation

[C:1]1([CH3:25])[CH:6]=[CH:5][C:4]([S:7]([CH2:10][CH2:11][O:12][C:13](=[O:24])[CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:26][S:27](O)(=[O:29])=[O:28]>C(Cl)Cl>[C:1]1([CH3:25])[CH:6]=[CH:5][C:4]([S:7]([CH2:10][CH2:11][O:12][C:13](=[O:24])[CH2:14][CH2:15][C:16]2[CH:21]=[C:20]([S:27]([Cl:26])(=[O:29])=[O:28])[CH:19]=[CH:18][C:17]=2[O:22][CH3:23])(=[O:8])=[O:9])=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 3-(2-methoxyphenyl)propionic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 59, 5.0 g, 13.8 mmol) and 5 mL of CH2Cl2 was added dropwise chlorosulfonic acid (8.0 g, 69.0 mmol, 5.0 eq) with ice-bath cooling. The mixture was stirred at 0° C. for 30 min. The resulting thick oil was poured onto crushed ice with vigorous stirring. The mixture was extracted with EtOAc. The organic layer was dried over MgSO4, and concentrated by evaporation to give a thick oil, which was purified by column chromatography (CH2Cl2) to yield 3-(5-chlorosulfonyl-2-methoxyphenyl)propionic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 60, 4.7 g, 74%) as a light brown oil.

Workup

temperaturecooling
additionThe resulting thick oil was poured
customonto crushed ice with vigorous stirring
extractionThe mixture was extracted with EtOAc
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated by evaporation
customto give a thick oil, which
customwas purified by column chromatography (CH2Cl2)

Sources & evidence

ORD record: ord-86dad9731fd04e88af6453b28a954570
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06897227B2

Reaction notes

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