Triethylamine → tert-butyl 4-[2,5-dioxo-1-(tetrahydro-2H-pyran-4-ylmethyl)-5-{5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1,3-thiazol-2-yl}pentyl]benzoate

HRID 1881835Notes

Reaction equation

HRID 1881835 reaction equation
[O:1]=[C:2]([CH:24]=[CH2:25])[CH:3]([C:11]1[CH:23]=[CH:22][C:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:13][CH:12]=1)[CH2:4][CH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[O:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[O:32][CH2:33][C:34]1[S:38][C:37]([CH:39]=[O:40])=[N:36][CH:35]=1.C(N(CC)CC)C>C(O)C.[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C>[O:1]=[C:2]([CH2:24][CH2:25][C:39](=[O:40])[C:37]1[S:38][C:34]([CH2:33][O:32][CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31][O:26]2)=[CH:35][N:36]=1)[CH:3]([C:11]1[CH:12]=[CH:13][C:14]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])=[CH:22][CH:23]=1)[CH2:4][CH:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 593313055-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1,3-thiazole-2-carbaldehydeHCID 59331470tert-butyl 4-[2-oxo-1-(tetrahydro-2H-pyran-4-ylmethyl)but-3-en-1-yl]benzoate

Product 1

HCID 59331421tert-butyl 4-[2,5-dioxo-1-(tetrahydro-2H-pyran-4-ylmethyl)-5-{5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1,3-thiazol-2-yl}pentyl]benzoateYield 95.2%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of tert-butyl 4-[2-oxo-1-(tetrahydro-2H-pyran-4-ylmethyl)but-3-en-1-yl]benzoate (1.50 g) in ethanol (15 mL) were added 5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1,3-thiazole-2-carbaldehyde (1.20 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (130 mg) and triethylamine (260 μL), and the mixture was stirred with heating under reflux for 4 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (2.37 g, yield 95%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS: 488 (MH+).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 4 hr
  3. washwashed with water
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b4f620fcf0314dfebc41d6ee4b66bedd
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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