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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Ethyl Acetate → Methanesulfonic acid (4S,5S)-5-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-YL)-methanesulfonyloxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

HRID 1268708
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HRID 1268708 반응식
[CH3:1][C:2]1([CH3:18])[O:6][C@@H:5]([C@@H:7]([C@@H:9]2[C@H:13]([CH2:14][OH:15])[O:12][C:11]([CH3:17])([CH3:16])[O:10]2)[OH:8])[CH2:4][O:3]1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>ClCCl.N1C=CC=CC=1>[CH3:1][C:2]1([CH3:18])[O:6][C@@H:5]([C@H:7]([O:8][S:20]([CH3:19])(=[O:22])=[O:21])[C@@H:9]2[C@H:13]([CH2:14][O:15][S:20]([CH3:19])(=[O:22])=[O:21])[O:12][C:11]([CH3:17])([CH3:16])[O:10]2)[CH2:4][O:3]1
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참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 13963403HCID 13963403, 화합물

생성물 1

HCID 11026162Methanesulfonic acid (4S,5S)-5-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-YL)-methanesulfonyloxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester수율 98%

시약·촉매·용매 2

HCID 1049Pyridine용매
HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

4.1 g (0.016 mol) of {(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4R,5S)-(5-hydroxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)-methanol from the aforementioned Experimental Example 2 were dissolved in a mixed solvent of 1.0 L dichloromethane and 25 mL pyridine. After cooling the mixture to 0° C., 18 mL (0.236 mol) of methanesulfonyl chloride were added and the resulting solution was stirred for 5 h at 0° C. Saturated sodium bicarbonate solution was added and the compound was extracted with chloroform. The extract was dried, filtered, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography using the eluant hexane:ethyl acetate=2:1 to obtain 6.4 g (yield: 98%) of methanesulfonic acid {(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4S,5S)-(5-methanesulfonyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)methyl ester as an oil.

후처리

  1. extractionthe compound was extracted with chloroform
  2. customThe extract was dried
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-68f747b8e65f449a8471b0a58b2e9cfe
출처 데이터셋
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07199127B2

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