Water → HCID 54397707, compound

HRID 1729105Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[C:6]([CH3:11])=[C:7]([CH3:10])[NH:8][CH:9]=1)=[O:4].[OH-].[Na+].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.O>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[C:6]([CH3:11])=[C:7]([CH3:10])[N:8]([S:20]([C:17]2[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=2)(=[O:22])=[O:21])[CH:9]=1)=[O:4]

Participants

Conditions

Temperature: 7.5 °C

Procedure

To a stirred solution of 2,3-dimethyl-1H-pyrrole-4-carboxylic acid methyl ester (Heterocycles 1977, 7, 77) (7.95 g, 51.9 mmol) in THF (160 mL) was added dropwise 50% NaOH (80 mL). The reaction mixture was stirred for 5 minutes and then a solution of p-toluenesulfonyl chloride (11.87 g, 62.3 mmol) in THF (160 mL) was added dropwise to the stirred mixture at room temperature. The mixture was stirred at room temperature for 30 minutes then cooled to 5 to 10° C. and treated dropwise with water (200 mL). The THF was evaporated in vacuo and the aqueous residue was thoroughly extracted with CH2Cl2. The organic extract was washed, dried (Na2SO4), and concentrated in vacuo. The residue was chromatographed over silica gel using toluene as eluant to give the required compound (13.6 g, 85%) as a pale yellow solid, m.p. 108°-114° C.

Workup

stirringThe mixture was stirred at room temperature for 30 minutes
customThe THF was evaporated in vacuo
extractionthe aqueous residue was thoroughly extracted with CH2Cl2
extractionThe organic extract
washwas washed
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe residue was chromatographed over silica gel

Sources & evidence

ORD record: ord-16a6bd56468743beb517fd4246be48c5
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05331006

Reaction notes

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