Hydrochloric Acid → 5-Cyclobutyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolecarboxylic acid

HRID 2423420노트

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HRID 2423420 반응식
[CH:1]1([C:5]2[O:9][N:8]=[C:7]([C:10]3[C:15]([Cl:16])=[CH:14][N:13]=[CH:12][C:11]=3[Cl:17])[C:6]=2[C:18]([O:20]CC)=[O:19])[CH2:4][CH2:3][CH2:2]1.O1CCCC1.[OH-].[Na+].Cl>CO>[CH:1]1([C:5]2[O:9][N:8]=[C:7]([C:10]3[C:11]([Cl:17])=[CH:12][N:13]=[CH:14][C:15]=3[Cl:16])[C:6]=2[C:18]([OH:20])=[O:19])[CH2:2][CH2:3][CH2:4]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59321470Ethyl 5-cyclobutyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolecarboxylate

생성물 1

HCID 593214695-Cyclobutyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolecarboxylic acid수율 88.1%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
120 °C

실험 절차

To a solution of ethyl 5-cyclobutyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolecarboxylate (1.00 g, 2.93 mmol), in 2:1 tetrahydrofuran:methanol (15 mL) was added 1 N aqueous sodium hydroxide (4.40 mL, 4.40 mmol). The solution was heated in a microwave reactor to 120° C. for 500 seconds. Then 1 N aqueous hydrochloric acid (4.40 mL, 4.40 mmol) was added and the solution was concentrated. Water was added and the mixture was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, concentrated and dried under a nitrogen stream at 45° C. overnight to afford 5-cyclobutyl-3-(3,5-dichloro-4-pyridinyl) -4-isoxazolecarboxylic acid (808 mg, 88%). 1H-NMR (400 MHz, DMSO-d6) δ 13.34 (br s, 1H), 8.81 (s, 2H), 4.33-4.25 (m, 1H), 2.42-2.32 (m, 4H), 2.15-2.05 (m, 1H), 1.96-1.88 (m, 1H).

후처리

  1. concentrationthe solution was concentrated
  2. additionWater was added
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customdried under a nitrogen stream at 45° C. overnight

출처 및 근거

ORD 기록
ord-bb22dc44e34047058028f05d7afe0d0f
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960552B2

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