A single vessel protocol for the efficient formation of amide bonds from esters and lactones

Tetrahedron Letters

Volumn 43, Issue 40, 2002, Pages 7221-7223

  Kawahata, Noriyuki H ^a   Brookes, Jeseca ^a   Makara, Gergely M ^a  

^a NeoGenesis Pharmaceuticals Inc   (United States)

Author keywords

Amide; Ester; Parallel; Polymer supported; Scavenger

Indexed keywords

AMIDE; CYANAMIDE; ESTER DERIVATIVE; LACTONE DERIVATIVE; RESIN; SCAVENGER;

ARTICLE; CHEMICAL BOND; EXTRACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; MASS SPECTROMETRY; THIN LAYER CHROMATOGRAPHY;

LETHRINIDAE;

EID: 0037201121     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01657-X     Document Type: Article

References (15)

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8. Macroporous 30-60 mesh, Aldrich.
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11. MP-Carbonate, 18-52 mesh, Argonaut Technologies.
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13. Typical procedure (3k): Methyl 4-bromobenzoate (0.02 mmol) was dissolved in THF (1 mL) and benzyltrimethylammonium hydroxide (0.04 mmol, 20% in MeOH) was added. The solution was heated (55°C) for 18 h. The mixture was cooled to rt and MP-TsOH (0.05 mmol) was added. The mixture was agitated at rt for 3 h. The reaction was diluted with THF (0.5 mL) and α,α-dimethyl-3-(p-F-phenyl)ethylamine (0.1 mmol) and 1-hydroxybenzotriazole (0.04 mmol) were added. PS-carbodiimide (0.08 mmol) was then added and the mixture was agitated for 18 h at rt. MP-carbonate resin (0.12 mmol) and MP-TsOH (0.12 mmol) resin were added and the mixture was agitated for 8 h. The mixture was filtered and the resin was washed with THF (1.5 mL). The filtrate was concentrated to give 3k (6.5 mg, 98%) in high purity (99% determined by ELSD-HPLC of the desired ion).
14. PS-Isocyanate, 100-200 mesh, Argonaut Technologies.
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