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

HRID 1492015Notes

Reaction equation

HRID 1492015 reaction equation
[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]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86748311HCID 86748311, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6e115fa6489946c9bf2f295262ec1269
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

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