Hydrochloric Acid → 4-(4-Fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

HRID 601849노트

반응식

HRID 601849 반응식
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][CH:7]2[C:14]3[CH:13]=[C:12]([C:15]([O:17]C)=[O:16])[N:11](S(C4C=CC(C)=CC=4)(=O)=O)[C:10]=3[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[OH-].[K+].[Li+].[OH-].Cl>C1COCC1.CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[C:14]3[CH:13]=[C:12]([C:15]([OH:17])=[O:16])[NH:11][C:10]=3[CH2:9][CH2:8]2)=[CH:29][CH:30]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 14797Potassium HydroxideHCID 59180148Methyl 4-(4-fluorobenzyl)-1-tosyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

생성물 1

HCID 591801514-(4-Fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

The title compound was synthesized from methyl 4-(4-fluorobenzyl)-1-tosyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate in two steps. First, the starting material's methyl ester was hydrolyzed according to General Procedure 7. In this case, 0.070 g (0.274 mmol) of starting ester and potassium hydroxide (10 M, 0.16 mL, 1.6 mmol) were used. The deprotected methyl ester (4-(4-fluorobenzyl)-1-tosyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid) (0.035 g, 0.13 mmol) was then dissolved in THF (3 mL) and MeOH (3 mL), and LiOH (0.055 g, 1.3 mmol) in H2O (3 mL) was added and the reaction stirred at 70° C. for 6 h. The reaction was diluted in 25 mL H2O and acidified to pH 2-3 with 1 N HCl, then extracted with 2×50 mL EtOAc. The organic layer was dried over Na2SO4, concentrated and purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-100% EtOAc/heptane to afford the title compound. 16 mg. 19F NMR δ ppm −102.42 (m, J=5.4) LCMS-MS (ESI−) 258.0 (M−H); HPLC (UV=98.52%), (ELSD=100%).

후처리

  1. extractionextracted with 2×50 mL EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by column chromatography (Isco CombiFlash)
  5. washeluting with a gradient of 0-100% EtOAc/heptane

출처 및 근거

ORD 기록
ord-909a791f00404e01a28d16a7a788dc26
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902252B2

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