p-Toluenesulfonic acid → HCID 53785033, compound

HRID 1439968Notes

Reaction equation

HRID 1439968 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20]([NH:22][C@@H:23]([CH2:31][CH2:32][CH2:33][OH:34])[C:24]([O:26]C(C)(C)C)=O)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1C=CC=CC=1.C(OCC)(=O)C>[CH2:12]([O:19][C:20]([NH:22][C@H:23]1[CH2:31][CH2:32][CH2:33][O:34][C:24]1=[O:26])=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 14565417tert-Butyl N-[(benzyloxy)carbonyl]-5-hydroxy-L-norvalinate

Product 1

HCID 53785033HCID 53785033, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In benzene (100 ml) was dissolved tert-butyl (S)-2-(N-benzyloxycarbonylamino)-5-hydroxyvalerate [synthesized by the method described in the Journal of Organic Chemistry, 55, 1711 (1990)](5.1 g) and following addition of p-toluenesulfonic acid (0.05 g), the mixture was stirred under reflux for 1 hour. This reaction mixture was diluted with ethyl acetate (100 ml) and washed with water, saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride in the order mentioned. After drying (MgSO4), the solvent was distilled off. The residue was chromatographed on a silica gel column and elution was carried out with ethyl acetate-hexane (1:2, v/v). From the eluate was obtained (S)-3-(N-benzyloxycarbonylamino)-2-oxotetrahydropyran (2.0 g, 51%) as an oil. NMR (δ ppm in CDCl3): 1.54-1.74 (1H, m), 1.96-2.10 (2H, m), 2.55-2.72 (1H, m), 4.36 (2H, t, J=6.2 Hz), 4.37-4.50 (1H, m), 5.13 (2H, s), 5.62 (1H, broad), 7.34-7.40 (5H, m). Optical rotation [α]D +51.5° (C=0.98, CHCl3)

Workup

  1. customsynthesized by the method
  2. temperatureunder reflux for 1 hour
  3. washwashed with water, saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride in the order
  4. dry with materialAfter drying (MgSO4)
  5. distillationthe solvent was distilled off
  6. customThe residue was chromatographed on a silica gel column and elution

Sources & evidence

ORD record
ord-0dbf66be4bd34541a068d470bc079a8c
Source dataset
uspto-grants-1996_03
Patent number
US05496834

Reaction notes

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