Hydrochloric Acid → HCID 118062621, compound

HRID 920780Notes

Reaction equation

HRID 920780 reaction equation
[F:1][CH2:2][C:3]1([C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])[CH2:6][C:5](OC)([O:7]C)[CH2:4]1.Cl>>[F:1][CH2:2][C:3]1([C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])[CH2:6][C:5](=[O:7])[CH2:4]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 118062488HCID 118062488, compound

Product 1

HCID 118062621HCID 118062621, compoundYield 62.3%

Procedure

To a stirred solution of Intermediate 302B (0.6 g, 2.56 mmol) was added a conc. aq. solution of HCl (1.576 mL, 20.49 mmol) and the reaction mass was stirred at RT for 16 h. The reaction was extracted with DCM (3×10 mL) and the organic layer was washed with water and a 10% aq. solution of NaHCO3, and then dried over Na2SO4, filtered and concentrated to afford Intermediate 302C as a pale yellow liquid (0.3 g, 62%). 1H NMR (400 MHz, chloroform-d) δ ppm 5.12 (s, 1H), 4.67-4.87 (m, 2H), 3.44-3.64 (m, 2H), 3.12-3.31 (m, 2H), 1.29 (d, J=6.53 Hz, 6H).

Workup

  1. extractionThe reaction was extracted with DCM (3×10 mL)
  2. washthe organic layer was washed with water
  3. dry with materiala 10% aq. solution of NaHCO3, and then dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b5ff6eb143c54664ad35744de83a50da
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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