Pyridine → (S)-6-benzoyloxy-3-oxo-5-hydroxyhexanoic acid tert-butylester

HRID 10129

反応式

HRID 10129 の反応式
[C:1]([O:5][C:6](=[O:15])[CH2:7][C:8](=[O:14])[CH2:9][C@H:10]([OH:13])[CH2:11][OH:12])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-].[Na+]>C(Cl)Cl.O>[C:1]([O:5][C:6](=[O:15])[CH2:7][C:8](=[O:14])[CH2:9][C@H:10]([OH:13])[CH2:11][O:12][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 11401693(5S)-5,6-dihydroxy-3-oxohexanoic tert-butyl ester

生成物 1

HCID 15099849(S)-6-benzoyloxy-3-oxo-5-hydroxyhexanoic acid tert-butylester収率 78%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 16.8 g (77 mmol) of the (5S)-5,6-dihydroxy-3-oxohexanoic tert-butyl ester produced in Example 1 in 120 mL of methylene chloride were added 11.2 mL of pyridine and 10.2 mL of benzoyl chloride at 0° C., and the mixture was stirred at 0° C. for 2 hours. After completion of the reaction, the reaction mixture was diluted with 38 mL of water and adjusted to pH 7 with 20% aqueous NaOH solution. The aqueous layer was separated and further extracted with 2 portions of methylene chloride, 120 mL each. The organic layers were combined and dehydrated over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to give an oil. This residue was purified by silica gel column chromatography (Kieselgel 60, product of Merck; hexane:acetone=5:1) to give 19.3 g of (5S)-6-benzoyloxy-5-hydroxy-3-oxohexanoic tert-butyl ester (white solid).

後処理

  1. customAfter completion of the reaction
  2. customThe aqueous layer was separated
  3. extractionfurther extracted with 2 portions of methylene chloride, 120 mL each
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto give an oil
  6. customThis residue was purified by silica gel column chromatography (Kieselgel 60, product of Merck; hexane:acetone=5:1)

出典と根拠

ORDレコード
ord-29050331286246aa9b5102f1f43d720f
出典データセット
uspto-grants-2006_08
特許番号
US07094594B2

関連ノート

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