Hydrochloric Acid → 4-(phenethylthio)-1H-pyrrole-2-carboxylic acid

HRID 1987923

Reaction equation

[CH2:1]([S:9][C:10]1[CH:11]=[C:12]([C:15]([O:17]C)=[O:16])[NH:13][CH:14]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[K+].Cl>CO.O>[CH2:1]([S:9][C:10]1[CH:11]=[C:12]([C:15]([OH:17])=[O:16])[NH:13][CH:14]=1)[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of methyl 4-(phenethylthio)-1H-pyrrole-2-carboxylate (233 mg, 0.890 mmol) and KOH (250 mg, 4.46 mmol) in MeOH (1.2 mL) and H2O (0.6 mL) was stirred at 60° C. for 1.5 h, cooled to 0° C., acidified with concentrated HCl and diluted with H2O. The solid precipitate was filtered, washed with H2O and air dried under vacuum to afford the title compound (81.0 mg) as a colorless solid that was used in the next step without purification: 1H NMR (400 MHz, CDCl3) δ 2.84-2.90 (m, 2H), 2.91-2.98 (m, 2H), 7.03-7.07 (m, 1H), 7.07-7.10 (m, 1H), 7.13-7.32 (m, 5H), 9.22 (br. s., 1 H); HPLC a) column: Phenomenex Luna 5μ 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% H3PO4 to 90% MeOH/10% H2O/0.1% H3PO4; 1 min hold, 4 mL/min UV detection at 220 nm, 3.293 min retention time, (95%); HPLC b) column: Phenomenex Luna C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold; 4 mL/min, UV detection at 220 nm, 3.258 min retention time; MS (ES): m/z 248.1 [M+H]+.

Workup

filtrationThe solid precipitate was filtered
washwashed with H2O and air
customdried under vacuum

Sources & evidence

ORD record: ord-4fa1e56aafe140099f3e3588af54398a
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07553836B2

Linked notes

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