Hydrochloric Acid → HCID 59132793, compound

HRID 1993082Notes

Reaction equation

HRID 1993082 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:32]=[CH:33][CH:34]=2)[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]([C:27]3[O:31][N:30]=[CH:29][CH:28]=3)[CH2:21][C:22]([O:24]CC)=[O:23])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.O.Cl>C(O)(=O)C>[F:36][C:2]([F:1])([F:35])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[C:11]([CH:32]=[CH:33][CH:34]=2)[CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([CH:20]([C:27]3[O:31][N:30]=[CH:29][CH:28]=3)[CH2:21][C:22]([OH:24])=[O:23])=[CH:18][CH:19]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962Water2×HCID 59132798HCID 59132798, compound

Product 1

HCID 59132793HCID 59132793, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compound 62.4 was dissolved in glacial acetic acid (1 mL) and water (0.3 mL) and heated to 95° C. for 16 h. 1N HCl (0.1 mL) was added and the reaction mixture was heated for another 16 h. The reaction mixture was poured into deionized water (50 mL) and extracted twice with diethyl ether. The combined organic layers were washed with saturated brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 5% methanol in dichloromethane eluant). Compound 62 was obtained as a thick oil (26 mg). LC-MS ESI (pos.) m/e: 468.1 (M+H). 1H NMR (500 MHz) (CDCl3) δ 8.14 (s, 1H); 7.70 (s, 4H); 7.66 (s, 1H); 7.56 (d, J=7.5 Hz, 1H); 7.50-7.45 (m, 2H); 7.22 (d, J=8.5 Hz, 2H); 6.96 (d, J=8.5, 2H); 5.99 (s, 1H); 5.12 (s, 2H); 4.67 (t, J=7.7 Hz, 1H); 4.08 (m, 2H); 3.16 (dd, J=16, 7.5 Hz, 1H); 2.95 (dd, J=16, 8.0 Hz, 1H); 1.17 (t, J=7.2 Hz, 3H).

Workup

  1. temperaturethe reaction mixture was heated for another 16 h
  2. extractionextracted twice with diethyl ether
  3. washThe combined organic layers were washed with saturated brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (silica gel, 5% methanol in dichloromethane eluant)

Sources & evidence

ORD record
ord-7ded9443d6ea4c9eacd44d1407aadf04
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Reaction notes

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