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

HRID 2420729

반응식

HRID 2420729 반응식
[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

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 67215046methyl 4-(phenethylthio)-1H-pyrrole-2-carboxylate

생성물 1

HCID 672152014-(phenethylthio)-1H-pyrrole-2-carboxylic acid수율 36.8%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매2회

반응 조건

온도
0 °C

실험 절차

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, 2 H), 2.91-2.98 (m, 2 H), 7.03-7.07 (m, 1 H), 7.07-7.10 (m, 1 H), 7.13-7.32 (m, 5 H), 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]+.

후처리

  1. filtrationThe solid precipitate was filtered
  2. washwashed with H2O and air
  3. customdried under vacuum

출처 및 근거

ORD 기록
ord-074251c477cb4ceca3ec2b6b4f23f668
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07956049B2

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