[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 546930ノート

反応式

HRID 546930 の反応式
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]

参加物

3

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21863450Trifluoroacetic acid methylene chloride溶媒

実験手順

[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%).

後処理

  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)

出典と根拠

ORDレコード
ord-18c493705eb847aa88898b24e78fa12f
出典データセット
uspto-grants-2011_05
特許番号
US07935688B2

反応ノート

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