Hydrochloric Acid → HCID 68671111, compound

HRID 2192938Notes

Reaction equation

HRID 2192938 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6](/[C:16](=[CH:29]\[C@H:30]3[CH2:50][CH2:49][C:32]4(O[C@H](C5C=CC=CC=5)[C@@H](C5C=CC=CC=5)[O:33]4)[CH2:31]3)/[C:17]([NH:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][N:21]=3)=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH2:3][CH2:2]1.[ClH:51].Cl.C(OCC)(=O)C>O1CCOCC1.[Cl-].[Na+].O.C(OCC)(=O)C>[ClH:51].[CH:1]1([C:4]2[CH:5]=[C:6](/[C:16](=[CH:29]\[C@H:30]3[CH2:50][CH2:49][C:32](=[O:33])[CH2:31]3)/[C:17]([NH:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][N:21]=3)=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:15][CH2:14]2)(=[O:11])=[O:12])[CH2:2][CH2:3]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 21866389Hydrogen chloride-ethyl acetateHCID 59570927HCID 59570927, compound

Product 1

HCID 68671111HCID 68671111, compound

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 6-({(2E)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(2R,3R,7S)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]prop-2-enoyl}amino)nicotinic acid (194 mg) in 1,4-dioxane (4 mL) was added 4 M hydrochloric acid (4 mL), followed by stirring at 50° C. for 2 hours. After leaving it to be cooled to room temperature, saturated brine was added thereto. After extraction with chloroform, the organic layer was dried over anhydrous magnesium sulfate. The crude product obtained by concentration was dissolved in ethyl acetate (4 mL), and 4 M hydrogen chloride/ethyl acetate (1 mL) was added thereto. It was stirred at room temperature for 30 minutes and concentrated. The obtained oily substance was solidified with diisopropyl ether and collected by filtration to obtain 6-({(2E)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(1S)-3-oxocyclopentyl]prop-2-enoyl}amino)nicotinic acid monohydrochloride (87 mg) as a white solid.

Workup

  1. customAfter leaving it
  2. temperatureto be cooled to room temperature
  3. extractionAfter extraction with chloroform
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customThe crude product obtained by concentration
  6. stirringIt was stirred at room temperature for 30 minutes
  7. concentrationconcentrated
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-064af9127caf43daab6ef5b0b8c3e78c
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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