Hydrochloric Acid → HCID 14167821, compound

HRID 487763Notes

Reaction equation

HRID 487763 reaction equation
[C:1]([NH:4][CH:5]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([CH3:15])[O:8][C:7](OC)([O:16]C)[CH2:6]1)(=[O:3])[CH3:2].O.Cl>CO>[O:16]=[C:7]1[CH2:6][CH:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]([C:11]([O:13][CH3:14])=[O:12])[CH:9]([CH3:15])[O:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 14167769HCID 14167769, compound

Product 1

HCID 14167821HCID 14167821, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-acetylamino-2,2-dimethoxy-6-methyl-3,4-dihydro-2H-pyran-5-carboxylate (13.7 g) (Example 23) in methanol (100 ml) at 20°-25° C. was added water (4.0 ml) and 1N HCl (0.4 ml). The mixture was stirred at 20°-25° C. for five hours, then the solvents were evaporated at reduced pressure and the residual gum (13 g) was redissolved in trifluoroacetic acid (100 ml), to which was added methylene chloride (25 ml) and triethylsilane (25 ml). The mixture was stirred at 20°-25° C. for 70 hours and then the solvents were evaporated at reduced pressure. The residue was purified by chromatography on K60 silica eluting with ethyl acetate to give methyl 2-oxo-4-acetylamino-6-methyl-3,4,5,6-tetrahydro-2H-pyran-5-carboxylate (4.0 g) m.p. 135°-6° C. (EtOAc/hexane) (4,5-trans: 5,6-trans isomer).

Workup

  1. customthe solvents were evaporated at reduced pressure
  2. dissolutionthe residual gum (13 g) was redissolved in trifluoroacetic acid (100 ml), to which
  3. additionwas added methylene chloride (25 ml) and triethylsilane (25 ml)
  4. stirringThe mixture was stirred at 20°-25° C. for 70 hours
  5. customthe solvents were evaporated at reduced pressure
  6. customThe residue was purified by chromatography on K60 silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-669074b6009f4fdcbc3d8ee08c499f06
Source dataset
uspto-grants-1994_03
Patent number
US05296613

Reaction notes

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