Diisopropylethylamine → HCID 67772568, compound

Participants

Reaction Steps

DIPEA (8.53 mL, 49.0 mmol) was added to a mixture of (S)-2-(tert-butoxycarbonylamino)propanoic acid (3.089 g, 16.33 mmol), which is commercially available, and TBTU (5.24 g, 16.33 mmol) in DCM (30 mL). Upon stirring at rt the mixture gradually became a clear solution. Azetidin-3-ol hydrochloride (2.68 g, 24.5 mmol) was added and the mixture was stirred over night. NaHCO3 (8% aq., 20 mL) was added. The organic layer was washed with NaHCO3 (8% aq., 3×60 mL). DCM (100 mL) was used for back extraction of the combined aqueous phases. Toluene was added and the combined organic layers were concentrated on the rotavapor over night (45° C. in waterbath) to give the title product (3.35 g, 84%,) as a transparent oil which solidified upon standing. Mixture of rotamers: 1H NMR (500 MHz, CD3OD) δ 1.21-1.27, 1.41-1.49, 3.7-3.83, 3.98-4.27, 4.41-4.47, 4.56-4.64.

Provenance & Evidence