2,2-Dimethoxypropane → 2-[(4R, 6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic tert-butyl ester

HRID 10132

반응식

HRID 10132 반응식
[C:1]([O:5][C:6](=[O:23])[CH2:7][CH:8]([OH:22])[CH2:9][C@H:10]([OH:21])[CH2:11][O:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:4])([CH3:3])[CH3:2].CO[C:26](OC)([CH3:28])[CH3:27].C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:23])[CH2:7][C@H:8]1[CH2:9][C@@H:10]([CH2:11][O:12][C:13](=[O:20])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:21][C:26]([CH3:28])([CH3:27])[O:22]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 64952,2-DimethoxypropaneHCID 516892Sodium BicarbonateHCID 21040752(5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester

생성물 1

HCID 101333842-[(4R, 6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic tert-butyl ester수율 72%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
20 °C

실험 절차

To a solution composed of 8.94 g (27.6 mmol) of (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester produced in Example 15, 35.8 mL of 2,2-dimethoxypropane, and 2.5 mL of methylene chloride was added 269 mg (1.4 mmol) of p-toluenesulfonic acid-1H2O, and the mixture was stirred at 20° C. for 4 hours, after which 500 mL of saturated sodium hydrogen carbonate solution was added. The aqueous layer was separated and further extracted with 2 portions of methylene chloride, 20 mL each, and the organic layers were combined. The combined solution was dehydrated over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to give a colorless oil. This residue was purified by silica gel column chromatography (Kieselgel 60, product of Merck; hexane:acetone=10:1) to give 7.24 g of 2-[(4R,6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic tert-butyl ester (white solid). Yield: 72%.

후처리

  1. customThe aqueous layer was separated
  2. extractionfurther extracted with 2 portions of methylene chloride, 20 mL each
  3. distillationthe solvent was distilled off under reduced pressure
  4. customto give a colorless oil
  5. customThis residue was purified by silica gel column chromatography (Kieselgel 60, product of Merck; hexane:acetone=10:1)

출처 및 근거

ORD 기록
ord-980177fca8a041c8ab1d3755eefdece6
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094594B2

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