Hydrochloric Acid → HCID 118062566, compound

HRID 920784Notes

Reaction equation

HRID 920784 reaction equation
[F:1][CH:2]([F:17])[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][CH:2]([F:17])[C:3]1([C:11]([O:13][CH:14]([CH3:15])[CH3:16])=[O:12])[CH2:4][C:5](=[O:7])[CH2:6]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 118061368HCID 118061368, compound

Product 1

HCID 118062566HCID 118062566, compoundYield 61.2%

Procedure

To a stirred solution of Intermediate 304B (300 mg, 1.189 mmol) was added a conc. aq. solution of HCl (0.457 mL, 5.94 mmol) and the reaction mass was stirred at RT for 48 h. The reaction was quenched with water and extracted with DCM (2×25 mL). The organic layer was washed with water, a 10% aq. solution of NaHCO3, dried over Na2SO4, filtered and the filtrate concentrated. The crude product was purified by silica gel chromatography (4 g REDISEP® column, eluting with 25% ethyl acetate in hexanes). Fractions containing the product were combined and evaporated to afford Intermediate 304C as a pale yellow liquid (150 mg, 61%). 1H NMR (400 MHz, chloroform-d) δ ppm 6.40 (s, 1H), 5.15 (s, 1H), 3.33-3.51 (m, 4H), 1.23-1.33 (m, 6H).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with DCM (2×25 mL)
  3. washThe organic layer was washed with water
  4. dry with materiala 10% aq. solution of NaHCO3, dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated
  7. customThe crude product was purified by silica gel chromatography (4 g REDISEP® column, eluting with 25% ethyl acetate in hexanes)
  8. additionFractions containing the product
  9. customevaporated

Sources & evidence

ORD record
ord-9178cd827faf4a6bba5052416baf5697
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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