Benzoic Acid → (1S,4aS,7aR)-7-(hydroxymethyl)-1-(methylcarbamoyloxy)-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester

HRID 1976372노트

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HRID 1976372 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]2[CH2:18][CH:17]=[CH:16][CH:7]2[CH:8]([O:11][C:12](=[O:15])[NH:13][CH3:14])[O:9][CH:10]=1)=[O:4].[C:19](O)(=[O:26])C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[C@H:6]2[CH2:18][CH:17]=[C:16]([CH2:19][OH:26])[C@@H:7]2[C@H:8]([O:11][C:12](=[O:15])[NH:13][CH3:14])[O:9][CH:10]=1)=[O:4]

참가 물질

5

반응물 3

HCID 243Benzoic AcidHCID 2724141Tetrabutylammonium FluorideHCID 867566731-(Methylcarbamoyloxy)-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester

생성물 1

HCID 57107324(1S,4aS,7aR)-7-(hydroxymethyl)-1-(methylcarbamoyloxy)-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester수율 98.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

28.5 g of the above (1S, 4aS, 7aR )-7-(tert-butyldiemthylsilyloxymethyl)-1-(methylcarbamoyloxy)-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester were dissolved in tetrahydrofuran followed by addition of 35 g of benzoic acid. Next, 143 ml of tetra-n-butylammonium fluoride (1.0 M, tetrahydrofuran solution) were dropped in followed by stirring for 24 hours at room temperature. The reaction mixture was then extracted with ethyl acetate. After washing the organic phase with saturated aqueous sodium bicarbonate and brine, it was dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain a colorless powder from the hexane-ether eluate in the form of (1S,4aS,7aR)-7-(hydroxy-methyl)-1-(methylcarbamoyloxy)-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester (20.0 g, yield: 98.4%). The physicochemical properties of this compound are described in Table 66, Compound No. I-315.

후처리

  1. extractionThe reaction mixture was then extracted with ethyl acetate
  2. washAfter washing the organic phase with saturated aqueous sodium bicarbonate and brine, it
  3. dry with materialwas dried over magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-3b59b4c262f44436a8acc50fd5538f92
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06225478B1

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