Triethylamine → HCID 178452054, compound

HRID 556700Notes

Reaction equation

HRID 556700 reaction equation
[C:1]([C:5]1[S:9][C:8](=[NH:10])[N:7]([CH2:11][CH:12]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[F:30][C:31]1[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][C:32]=1[C:33](Cl)=[O:34]>O1CCCC1>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:33](=[O:34])[C:32]2[CH:36]=[C:37]([C:40]([F:41])([F:42])[F:43])[CH:38]=[CH:39][C:31]=2[F:30])/[N:7]([CH2:11][CH:12]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27348802-Fluoro-5-(trifluoromethyl)benzoyl ChlorideHCID 66660694tert-butyl 3-((5-tert-butyl-2-iminothiazol-3(2H)-yl)methyl)azetidine-1-carboxylate

Product 1

HCID 178452054HCID 178452054, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the product of Example 42A (4.1 g, 12.5 mmol) in tetrahydrofuran (40 mL) was added triethylamine (5.2 mL, 37.6 mmol) followed by 2-fluoro-5-(trifluoromethyl)benzoyl chloride (2.0 mL, 13.2 mmol). This mixture was warmed to 50° C. and was allowed to stir for 90 min then the mixture was cooled to ambient temperature and was stirred for 16 h. The mixture was quenched with saturated, aqueous NH4Cl (20 mL) and diluted with ethyl acetate (20 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organics were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography (SiO2, 60% hexanes in ethyl acetate) to give the title compound (5.2 g, 10.0 mmol, 80% yield). MS (DCI/NH3) m/z 516 (M+H)+.

Workup

  1. temperaturethe mixture was cooled to ambient temperature
  2. stirringwas stirred for 16 h
  3. customThe mixture was quenched with saturated, aqueous NH4Cl (20 mL)
  4. additiondiluted with ethyl acetate (20 mL)
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (3×10 mL)
  7. dry with materialThe combined organics were dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude material was purified by column chromatography (SiO2, 60% hexanes in ethyl acetate)

Sources & evidence

ORD record
ord-988091fe9c3a46e1a98f95c78efad551
Source dataset
uspto-grants-2011_11
Patent number
US08058293B2

Reaction notes

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