Hydrochloric Acid → 6-[3-Pentyl-3-(5,5,8,8-Tetramethyl-5,6,7,8-Tetrahydro-Naphthalen-2-yl)-Ureido]-Nicotinic Acid

HRID 1759786노트

반응식

HRID 1759786 반응식
[CH2:1]([N:6]([C:20]1[CH:29]=[CH:28][C:27]2[C:26]([CH3:31])([CH3:30])[CH2:25][CH2:24][C:23]([CH3:33])([CH3:32])[C:22]=2[CH:21]=1)[C:7](=[O:19])[NH:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][N:10]=1)[CH2:2][CH2:3][CH2:4][CH3:5].O.[OH-].[Li+].Cl>C1COCC1.CO.O>[CH2:1]([N:6]([C:20]1[CH:29]=[CH:28][C:27]2[C:26]([CH3:31])([CH3:30])[CH2:25][CH2:24][C:23]([CH3:32])([CH3:33])[C:22]=2[CH:21]=1)[C:7](=[O:19])[NH:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 22600033HCID 22600033, 화합물

생성물 1

HCID 102250846-[3-Pentyl-3-(5,5,8,8-Tetramethyl-5,6,7,8-Tetrahydro-Naphthalen-2-yl)-Ureido]-Nicotinic Acid수율 47.4%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

A solution of methyl 6-[3-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-nicotinate (55) (37 mg) in 5 mL THF, 2 mL methanol and 2 mL water was treated with lithium hydroxide hydrate (50 mg), stirred at room temperature for two hours. The reaction mixture was diluted with 5 mL water, the pH adjusted to 2 with concentrated HCl and extracted with three 10 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) followed by trituration in hexanes, yielding 17 mg 6-[3-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl) -ureido]-nicotinic acid (49) as a white solid. M.P. 175-179.5° C.

후처리

  1. extractionextracted with three 10 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-1d447a9423984400b7edb96721ccede6
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06838472B2

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