[4'-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2'-methyl-biphenyl-3-yl]-acetic Acid Methyl Ester → (4'-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-2'-methyl-biphenyl-3-yl)-acetic Acid

HRID 546930노트

반응식

HRID 546930 반응식
C[O:2][C:3](=[O:45])[CH2:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH:30]([O:35][Si](C(C)(C)C)(C)C)[C:31]([CH3:34])([CH3:33])[CH3:32])=[C:24]([CH3:43])[CH:23]=3)([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:13][C:12]=2[CH3:44])[CH:8]=[CH:9][CH:10]=1>ClCCl.FC(F)(F)C(O)=O>[CH2:18]([C:17]([C:14]1[CH:15]=[CH:16][C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([CH2:4][C:3]([OH:45])=[O:2])[CH:6]=2)=[C:12]([CH3:44])[CH:13]=1)([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH:30]([OH:35])[C:31]([CH3:33])([CH3:34])[CH3:32])=[C:24]([CH3:43])[CH:23]=1)[CH2:20][CH3:21])[CH3:19]

참가 물질

3

반응물 1

HCID 57708909[4'-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2'-methyl-biphenyl-3-yl]-acetic Acid Methyl Ester

생성물 1

HCID 15941706(4'-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-2'-methyl-biphenyl-3-yl)-acetic Acid수율 80.6%

시약·촉매·용매 1

HCID 21863450Trifluoroacetic acid methylene chloride용매

실험 절차

[4′-(1-{4-[3-(t-Butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2′-methyl-biphenyl-3-yl]-acetic acid methyl ester (Example 66-(1); 36 mg, 0.057 mmol) was dissolved in dichloromethane/trifluoroacetic acid=1/5 (1 mL), and the solution was stirred at room temperature for three hours. The reaction mixture was concentrated under reduced pressure, and then the residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=1/1). The product was dissolved in methanol/tetrahydrofuran=1/1 (1 mL). A 1 N sodium hydroxide aqueous solution (0.1 mL) was added, and the mixture was stirred at room temperature for one hour. A 30% sodium dihydrogenphosphate aqueous solution (0.3 mL) was added to the reaction mixture, and then the reaction mixture was concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/ethyl acetate=1/1) to give the title compound (23 mg, 80%).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=1/1)
  3. dissolutionThe product was dissolved in methanol/tetrahydrofuran=1/1 (1 mL)
  4. additionA 1 N sodium hydroxide aqueous solution (0.1 mL) was added
  5. stirringthe mixture was stirred at room temperature for one hour
  6. additionA 30% sodium dihydrogenphosphate aqueous solution (0.3 mL) was added to the reaction mixture
  7. concentrationthe reaction mixture was concentrated under reduced pressure
  8. customThe residue was purified by preparative TLC (hexane/ethyl acetate=1/1)

출처 및 근거

ORD 기록
ord-18c493705eb847aa88898b24e78fa12f
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935688B2

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