Hydrochloric Acid → methyl (Z)-(2S,3S,4S)-7-[4-hydroxy-2-(3-pyridyl)-tetrahydrofuran-3-yl]-4-heptenoate

HRID 1492015노트

반응식

HRID 1492015 반응식
[Si]([O:8][C@@H:9]1[CH2:13][O:12][C@H:11]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C@@H:10]1[CH2:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])(C(C)(C)C)(C)C.Cl>CO>[OH:8][C@@H:9]1[CH2:13][O:12][C@H:11]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C@H:10]1[CH2:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 86748311HCID 86748311, 화합물

생성물 1

HCID 86748312methyl (Z)-(2S,3S,4S)-7-[4-hydroxy-2-(3-pyridyl)-tetrahydrofuran-3-yl]-4-heptenoate수율 88.8%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 25.7 g (0.0612 mol) of methyl (Z)-(2S,3S,4S)-7-[4-(t-butyldimethylsilyloxy)-2-(3-pyridyl)tetrahydrofuran-3-yl]-4-heptenoate in 257 ml of methanol is bubbled with HCl gas for about 2 min to give a strongly acidic solution. The mixture is allowed to stand at 0° C. overnight and evaporated. The residue is dissolved in 100 ml of water and extracted with ethyl acetate (2×). The ethyl acetate extracts are discarded. The aqueous layer is diluted with 150 ml of methylene chloride and neutralized by portionwise addition of potassium carbonate. The layers are separated and the aqueous layer is extracted with methylene chloride (3×). The combined extracts are washed with brine, dried (MgSO4) and evaporated to give 16.6 g of methyl (Z)-(2S,3S,4S)-7-[4-hydroxy-2-(3-pyridyl)-tetrahydrofuran-3-yl]-4-heptenoate as an oil with elemental analysis: C,65.87; H,7.78; N,4.58 (theory: C,66.86; H, 7.59; N,4.58) and optical rotation [α]D 25=+9.44 (methanol) and mass spectrum m/z 306 (M+1) (cald. MW=305.38).

후처리

  1. customto give a strongly acidic solution
  2. customevaporated
  3. dissolutionThe residue is dissolved in 100 ml of water
  4. extractionextracted with ethyl acetate (2×)
  5. additionThe aqueous layer is diluted with 150 ml of methylene chloride
  6. additionneutralized by portionwise addition of potassium carbonate
  7. customThe layers are separated
  8. extractionthe aqueous layer is extracted with methylene chloride (3×)
  9. washThe combined extracts are washed with brine
  10. dry with materialdried (MgSO4)
  11. customevaporated

출처 및 근거

ORD 기록
ord-6e115fa6489946c9bf2f295262ec1269
출처 데이터셋
uspto-grants-1994_12
특허 번호
US05371096

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