Hydrochloric Acid → HCID 22558919, compound

HRID 2378562Notes

Reaction equation

HRID 2378562 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[C:13]([CH2:25][CH2:26][C:27]([O:29]CC)=[O:28])[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22]C[CH2:20]3)[CH:8]=[CH:7][C:5]=2[N:6]=1.Cl.FC1C=C(CCC(O)=O)C=CC=1[O:40]C>C(O)C>[CH:19]1([CH2:18][O:17][C:16]2[CH:15]=[CH:14][C:13]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:12][C:11]=2[C:9]2[CH:8]=[CH:7][C:5]3[NH:6][C:2](=[O:40])[S:3][C:4]=3[CH:10]=2)[CH2:24][CH2:23][CH2:22][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 30179663-(3-Fluoro-4-methoxyphenyl)propionic acidHCID 22558994HCID 22558994, compound

Product 1

HCID 22558919HCID 22558919, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of Intermediate 76 (202 mg) in ethanol (8 ml) was added with 5 N aqueous hydrochloric acid (1.5 ml), and stirred at 80° C. for 18.5 hours. The reaction mixture was concentrated under reduced pressure, and added with water (20 ml) and ethyl acetate (80 ml) for extraction. The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was added with 2 N aqueous sodium hydroxide (1.0 ml), reacted and treated according to the procedure described in the synthesis method of Intermediate 9 provided that the reaction was carried out for 2 hours to obtain the title compound (Compound No. V-89, 250 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionadded with water (20 ml) and ethyl acetate (80 ml) for extraction
  3. washThe organic layer was washed with saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. additionThe residue was added with 2 N aqueous sodium hydroxide (1.0 ml)
  7. customreacted
  8. additiontreated
  9. customprovided that the reaction
  10. waitwas carried out for 2 hours

Sources & evidence

ORD record
ord-9ccc219e59f04af68c9898b71f0092cc
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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