Triethylamine → HCID 10379776, compound

To a stirred solution of (S)-tert-butyl(1-hydroxy-4-methylpentan-2-yl)carbamate (1.6 g, 7.36 mmol) in dichloromethane (15 mL) was added triethyl amine (2.052 mL, 14.73 mmol) at 0° C. and the solution was stirred for 5 min. To this mixture at 0° C. was added methanesulfonyl chloride (0.574 mL, 7.36 mmol) dropwise and the reaction mixture was stirred at room temperature for 1 h. The reaction was quenched with water (15 mL) and extracted with DCM (2×15 mL). The combined organic layers were washed with brine (10 mL), dried over sodium sulphate, concentrated under reduced pressure to yield (S)-2-((tert-butoxycarbonyl)amino)-4-methylpentyl methanesulfonate (1.7 g, 5.75 mmol, 78% yield) as a yellow solid which was carried on without further purification. 1H NMR (400 MHz, CDCl3) δ 4.55 (m, 1 H), 4.25 (m, 1 H), 4.16 (m, 1 H), 3.92 (m, 1 H), 3.05 (s, 3 H), 1.66 (m, 2 H), 1.56 (m, 10 H), 0.92 (m, 6 H).

1. stirringthe reaction mixture was stirred at room temperature for 1 h
2. customThe reaction was quenched with water (15 mL)
3. extractionextracted with DCM (2×15 mL)
4. washThe combined organic layers were washed with brine (10 mL)
5. dry with materialdried over sodium sulphate
6. concentrationconcentrated under reduced pressure

ORD record

ord-7495700707474fb798e450ed3080ee7b

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703953B2