Hydrochloric Acid → HCID 86636542, compound

HRID 661451Notes

Reaction equation

HRID 661451 reaction equation
Cl.[CH2:2]([O:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=2)[CH2:10][CH2:9][C:8]1([NH:23][CH:24]1[N:29]([CH:30]([C:37]([F:40])([F:39])[F:38])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:28][C:27]([CH:53]([C:60]([F:63])([F:62])[F:61])[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)([O:41][CH2:42][CH2:43][CH2:44][CH2:45][C:46]([O:48]C(C)(C)C)=[O:47])[CH:26]=[N:25]1)[CH2:21][CH3:22])=[O:6])[CH3:3].O.C(OCC)(=O)C>C(O)(=O)C>[CH2:2]([O:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([F:19])([F:20])[F:18])=[CH:14][CH:15]=2)[CH2:10][CH2:9][C:8]1([NH:23][CH:24]1[N:29]([CH:30]([C:37]([F:40])([F:38])[F:39])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:28][C:27]([CH:53]([C:60]([F:61])([F:62])[F:63])[C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=2)([O:41][CH2:42][CH2:43][CH2:44][CH2:45][C:46]([OH:48])=[O:47])[CH:26]=[N:25]1)[CH2:21][CH3:22])=[O:6])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 86636543HCID 86636543, compound

Product 1

HCID 86636542HCID 86636542, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

5N HCl (0.5 ml) was added to a solution of the compound obtained in Example 6 (250 mg) in acetic acid (1.5 ml) and the mixture was stirred at 50° C. for 3 hours. The reaction mixture was cooled to room temperature, water and ethyl acetate was added to the mixture and the organic layer was separated, washed with a saturated aqueous sodium hydrogen carbonate solution three times and then with a saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (silica gel; hexane:ethyl acetate=4:1→1:1) to give the titled compound (183 mg). MS (m/z): 737 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe organic layer was separated
  3. washwashed with a saturated aqueous sodium hydrogen carbonate solution three times
  4. dry with materialwith a saturated brine, dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (silica gel; hexane:ethyl acetate=4:1→1:1)

Sources & evidence

ORD record
ord-687f71d073884568b2ab1048ff704961
Source dataset
uspto-grants-2011_12
Patent number
US08084611B2

Reaction notes

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