Hydrochloric Acid → HCID 117970123, compound

HRID 2271312Notes

Reaction equation

HRID 2271312 reaction equation
[CH3:1][C:2]1[C:6](=[O:7])[O:5][CH:4]([O:8]/[CH:9]=[C:10]2/[C:11](=[O:24])[N:12](C(OC(C)(C)C)=O)[CH2:13][CH2:14][CH2:15][CH2:16]/2)[CH:3]=1.Cl>ClCCl>[CH3:1][C:2]1[C:6](=[O:7])[O:5][CH:4]([O:8]/[CH:9]=[C:10]2/[C:11](=[O:24])[NH:12][CH2:13][CH2:14][CH2:15][CH2:16]/2)[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 117970125HCID 117970125, compound

Product 1

HCID 117970123HCID 117970123, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Tert-butyl (3E)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylene]-2-oxo-azepane-1-carboxylate I-13b (0.55 g) was solved in dichloromethane (20 mL) and hydrogen chloride (2.0378 mL, 4M in dioxane) was added dropwise. After 30 min., dichloromethane was added and the reaction mixture was washed with sat. NaHCO3. The aqueous layer was extracted once with dichloromethane, the organic layers were combined, dried over Na2SO4 and the solvent was evaporated to give the crude as a yellow solid. The residue was triturated in tertbutylmethylether and the solid was filtered and dried to give (3E)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylene]azepan-2-one Ia-13 (0.245 g, 63%) as a white solid. LCMS (Method D): 0.67 min; ES+238 (M+H+).

Workup

  1. washthe reaction mixture was washed with sat. NaHCO3
  2. extractionThe aqueous layer was extracted once with dichloromethane
  3. dry with materialdried over Na2SO4
  4. customthe solvent was evaporated
  5. customto give the crude as a yellow solid
  6. customThe residue was triturated in tertbutylmethylether
  7. filtrationthe solid was filtered
  8. customdried

Sources & evidence

ORD record
ord-e1c3d8a831454e3c89102377f466ecaf
Source dataset
uspto-grants-2015_09
Patent number
US09119398B2

Reaction notes

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