3-[1,3]DIOXOLAN-2-YL-PROPIONICACID

A mixture of amide 20 (3.23 g, 11.9 mmol, 1 equiv), DMAP (3.63 g, 29.7 mmol, 2.5 equiv), and carboxylic acid 16 (2.44 g, 16.7 mmol, 1.4equiv) in toluene (60 mL) was treated with DIPEA (3.52 mL, 20.2mmol, 1.7 equiv) and 2, 4, 6-trichlorobenzoyl chloride (3.72 mL, 23.8mmol, 2 equiv). The mixture was stirred for 4 h at r.t., the reaction was quenched with H2O (40 mL), and the mixture was extracted with EtOAc (3 × 20 mL). The organic layers were combined, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified byflash chromatography [silica gel, EtOAc-PE (8:2)] to give a colorlessoil; yield: 3.47 g (73%); Rf = 0.32 (EtOAc-cyclohexane, 9:1).DIPEA (145 muL, 0.83 mmol, 1.7 equiv) and 2, 4, 6-trichlorobenzoyl chloride(153 muL, 0.98 mmol, 2 equiv) were added to a mixture of amide15 (126 mg, 0.49 mmol, 1 equiv), DMAP (150 mg, 1.23 mmol, 2.5equiv), and carboxylic acid 16 (100 mg, 0.68 mmol, 1.4 equiv) in toluene(2.7 mL). The mixture was stirred overnight at r.t., the reaction was quenched with H2O (10 mL), and the mixture was extracted withEtOAc (3 × 5 mL). The organic layers were combined, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified byflash chromatography [silica gel, EtOAc-PE (7:3)] to give a colorlessoil; yield: 165 mg (87%); Rf = 0.25 (EtOAc-cyclohexane, 9:1).

Molecular Weight:146.14
XLogP3:-0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:146.05790880
Monoisotopic Mass:146.05790880
Topological Polar Surface Area:55.8
Heavy Atom Count:10
Complexity:117
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes