4-Chlorobenzoyl chloride → HCID 67772465, compound

Participants

Reaction Steps

TEA (4.73 mL, 34.1 mmol) was added to (S)-3-methyl-2-(methylamino)butan-1-ol (Compound B2.1) (1 g, 8.5 mmol) in DCM (10 mL). The mixture was cooled on an ice-bath and 4-chlorobenzoyl chloride (3.14 g, 17.9 mmol) in DCM (10 mL) was dropwise (over 10 min) added. The resultant mixture was stirred at rt for 2 h. The organic phase was washed with Na2CO3 (8 wt %, 40 mol) and concentrated under reduced pressure to give the title compound (3.3 g, 98%). The obtained crude product was used without further purification. LCMS (M+H)+: 394. Mixture of rotamers: 1H NMR (600 MHz, CD3OD) δ 0.93-1.04 (m), 1.13 (d), 1.98-2.13 (m), 2.87 (s), 3.02 (s), 3.60-3.74 (m), 4.43-4.73 (m), 7.16-7.64 (m), 7.87-8.19 (m). Total number of protons: 21.

Provenance & Evidence