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 2181762노트

반응식

HRID 2181762 반응식
[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]

참가 물질

7

반응물 4

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 69507500HCID 69507500, 화합물

생성물 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

시약·촉매·용매 2

HCID 962Water용매2회HCID 21881883Oxolane--water (1/1)용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3ee9c1f362de459b94fe9154b8b32b4c
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06893859B2

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