Hydrochloric Acid → HCID 67071421, compound

HRID 874235Notes

Reaction equation

HRID 874235 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:38])/[CH:5]=[CH:6]/[C:7]1[CH:8]=[C:9]2[C:34](=[CH:35][CH:36]=1)[O:33][C:12]1([CH2:16][CH2:15][N:14](C(=O)[C@H](C3C=CC4C(=CC=C(OC)C=4)C=3)C)[CH2:13]1)[CH2:11][C:10]2=[O:37].O>CC(O)=O>[CH3:2][O:3][C:4](=[O:38])/[CH:5]=[CH:6]/[C:7]1[CH:8]=[C:9]2[C:34](=[CH:35][CH:36]=1)[O:33][C:12]1([CH2:16][CH2:15][NH:14][CH2:13]1)[CH2:11][C:10]2=[O:37]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 67071675HCID 67071675, compound

Product 1

HCID 67071421HCID 67071421, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

HCl 20% aq. (5 ml, 30 mmol) was added to a suspension of (+)-(E)-3-[1′-[(S)-2-(6-methoxynaphthalen-2-yl)propanoyl]-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid methyl ester (926 mg, 1.85 mmol) in glacial AcOH (5 ml). The mixture was stirred in the microwave oven at 120° C. for 3 h. Water (5 ml) was added and the reaction mixture was extracted three times with DCM. The aqueous phase was evaporated under vacuum. MeOH (25 ml) and a catalytic amount of H2SO4 were added and the mixture was heated to 70° C. overnight. The solution was poured into water and NH3 was added to adjust the pH value to 9-10. The aqueous phase was extracted with DCM, dried over Na2SO4 and filtered. The solvent was evaporated to give (+)-(E)-3-[4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid methyl ester (210 mg) as a yellow oil (free base).

Workup

  1. extractionthe reaction mixture was extracted three times with DCM
  2. customThe aqueous phase was evaporated under vacuum
  3. additionMeOH (25 ml) and a catalytic amount of H2SO4 were added
  4. temperaturethe mixture was heated to 70° C. overnight
  5. additionThe solution was poured into water and NH3
  6. additionwas added
  7. extractionThe aqueous phase was extracted with DCM
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customThe solvent was evaporated

Sources & evidence

ORD record
ord-88c9a12c32a04938882429b27bd0e805
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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