Triethylamine → HCID 59331321, compound

HRID 1882019Notes

Reaction equation

HRID 1882019 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:18][C@H:19]3[CH2:39][CH2:38][C:21]4([O:25][C@H:24]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C@@H:23]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[O:22]4)[CH2:20]3)[C:14](=O)[CH:15]=[CH2:16])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[S:40]1[CH:44]=[CH:43][N:42]=[C:41]1[CH:45]=O.C([N:49](CC)CC)C.C([O-])(=O)C.[NH4+]>C(O)C.[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.CN(C)C=O.C(OCC)(=O)C.O>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:14]3[NH:49][C:45]([C:41]4[S:40][CH:44]=[CH:43][N:42]=4)=[CH:16][CH:15]=3)[CH2:18][C@H:19]3[CH2:39][CH2:38][C:21]4([O:25][C@H:24]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C@@H:23]([C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=5)[O:22]4)[CH2:20]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

10

Reactant 4

HCID 8471TriethylamineHCID 517165Ammonium AcetateHCID 27349031,3-Thiazole-2-carbaldehydeHCID 59331254HCID 59331254, compound

Product 1

HCID 59331321HCID 59331321, compoundYield 5%

Reagents, catalysts & solvents 5

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-[4-(cyclopropylsulfonyl)phenyl]-5-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]pent-1-en-3-one (1.70 g) in ethanol (10 mL) were added 1,3-thiazole-2-carbaldehyde (0.33 mL), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (93 mg) and triethylamine (0.19 mL), and the mixture was heated under reflux for 12 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-60:40, volume ratio) to give a colorless oil. To a solution of the obtained oil in N,N-dimethylformamide (20 mL) was added ammonium acetate (820 mg), and the mixture was stirred at 100° C. for 1.5 hr. The reaction mixture was diluted with ethyl acetate, washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=10:90-80:20, volume ratio) to give the title compound (0.100 g, yield 5%) as a colorless oil. MS: 637 (MH+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-60:40, volume ratio)
  8. customto give a colorless oil
  9. washwashed successively with water and saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=10:90-80:20, volume ratio)

Sources & evidence

ORD record
ord-3e583071dff145a4bb56eb9374056928
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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