Hydrogen Peroxide → (2S,3S,6R,7S,8S)-5-oxo-3-(triethylsilyloxy)-2,4,4,6,8-pentamethyl-7-(2,2,2-trichloroethoxycarbonyloxy)-10-undecenoic acid

HRID 2181762ノート

反応式

HRID 2181762 の反応式
[O:1]=[C:2]([C@H:32]([CH3:48])[C@@H:33]([O:39][C:40]([O:42][CH2:43][C:44]([Cl:47])([Cl:46])[Cl:45])=[O:41])[C@@H:34]([CH3:38])[CH2:35][CH:36]=[CH2:37])[C:3]([CH3:31])([CH3:30])[C@@H:4]([O:22][Si:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25])[C@H:5]([CH3:21])[C:6](N1[C@@H](CC2C=CC=CC=2)COC1=O)=[O:7].OO.[OH-].[Li+].S([O-])([O-])=[O:54].[Na+].[Na+]>C1COCC1.O.O>[O:1]=[C:2]([C@H:32]([CH3:48])[C@@H:33]([O:39][C:40]([O:42][CH2:43][C:44]([Cl:47])([Cl:46])[Cl:45])=[O:41])[C@@H:34]([CH3:38])[CH2:35][CH:36]=[CH2:37])[C:3]([CH3:30])([CH3:31])[C@@H:4]([O:22][Si:23]([CH2:28][CH3:29])([CH2:24][CH3:25])[CH2:26][CH3:27])[C@H:5]([CH3:21])[C:6]([OH:7])=[O:54]

参加物

7

反応物 4

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 69507500HCID 69507500、化合物

生成物 1

HCID 86586617(2S,3S,6R,7S,8S)-5-oxo-3-(triethylsilyloxy)-2,4,4,6,8-pentamethyl-7-(2,2,2-trichloroethoxycarbonyloxy)-10-undecenoic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 21881883Oxolane--water (1/1)溶媒

実験手順

A solution of (4S)-3 -[(2S,3S,6R,7S,8S)-5-oxo-3-(triethylsilyloxy)-2,4,4,6,8-pentamethyl-7-(2,2,2-trichloroethoxycarbonyloxy)-10-undecenoyl]-4-benzyloxazolidinone (21.5 g) in 125 mL of 4:1 THF/water is cooled on ice and treated with 10.2 mL of 30% H2O2 followed by a solution of lithium hydroxide (0.96 g) in 50 mL of water. After 1 hour, a solution of sodium sulfite (12.6 g) in 75 mL of water is added, and the mixture is adjusted to pH 3 and concentrated under vacuum. The resulting slurry is extracted with ethyl acetate. The extract is washed with brine, dried over MgSO4, filtered, and evaporated. The product is purified by chromatography on SiO2.

後処理

  1. concentrationconcentrated under vacuum
  2. extractionThe resulting slurry is extracted with ethyl acetate
  3. washThe extract is washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe product is purified by chromatography on SiO2

出典と根拠

ORDレコード
ord-3ee9c1f362de459b94fe9154b8b32b4c
出典データセット
uspto-grants-2005_05
特許番号
US06893859B2

反応ノート

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