Hydrochloric Acid → 4-[1-Pentyl-3-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic Acid

HRID 1759782노트

반응식

HRID 1759782 반응식
[CH2:1]([N:6]([C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=1)[C:7]([NH:9][C:10]1[CH:19]=[CH:18][C:17]2[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]([CH3:23])([CH3:22])[C:12]=2[CH:11]=1)=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5].O.[OH-].[Li+].Cl>C1COCC1.CO.O>[CH2:1]([N:6]([C:24]1[CH:25]=[CH:26][C:27]([C:28]([OH:30])=[O:29])=[CH:32][CH:33]=1)[C:7]([NH:9][C:10]1[CH:19]=[CH:18][C:17]2[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]([CH3:22])([CH3:23])[C:12]=2[CH:11]=1)=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5]

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 22600038Methyl 4-[1-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate

생성물 1

HCID 101602244-[1-Pentyl-3-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic Acid수율 40.7%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of methyl 4-[1-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (190 mg) in 20 mL THF, 5 mL methanol 5 mL water was treated with lithium hydroxide hydrate (0.3 g) and stirred at room temperature for two hours. The mixture was diluted with 20 mL water, the pH adjusted to 2 with concentrated HCl and extracted with three 25 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo, to give a pale yellow solid. The product was purified by flash chromatography (SiO2, 10% methanol/dichloromethane), to yield 75 mg of 4-[1-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic acid (42) as a white solid. M.P.: 201-202° C.

후처리

  1. extractionextracted with three 25 mL portions of ethyl acetate
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a pale yellow solid
  6. customThe product was purified by flash chromatography (SiO2, 10% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-6ac8b75ef90040c19f9c2db2f50483b3
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06838472B2

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