Tert-Butyl hypochlorite → HCID 44465318, compound

Temperature

0 °C

A solution of (4-amino-4-methylpentyl)trimethylphosphonium chloride hydrochloride (0.70 g, 2.82 mmol) in a mixture of methanol (20 mL) and water (10 mL) was cooled in an ice bath for 15 min. t-BuOCl (1.0 mL, 3.0 equiv, 8.5 mmol) was added in one portion via syringe to the colorless solution to give a deep yellow solution. The reaction mixture was stirred for 30 min at 0° C., then room temperature for 30 min. The methanol was removed under reduced pressure and the aqueous solution was purified via reverse phase chromatography on a Shimadzu Prep-LC utilizing water/methanol and 0.05% acetic acid as modifier. Fractions were collected using UV absorbance at 215 nm. Fractions were pooled frozen and lyophilized to give a pale yellow solid (0.654 g, 82.6%). 1H NMR (D2O, 400 MHz): δ 1.40 (s, 6H), 1.65-1.69 (m, 2H), 1.85-1.89 (d, J=14.4, 9H), 1.89-1.92 (m, 2H), 2.19-2.27 (m, 2H). LRMS (ESI+) for C9H21Cl2NP+ (244.1); Found: 244, 246 (M+, M2H+)

1. additionwas added in one portion via syringe to the colorless solution
2. customto give a deep yellow solution
3. waitroom temperature for 30 min
4. customThe methanol was removed under reduced pressure
5. customthe aqueous solution was purified via reverse phase chromatography on a Shimadzu Prep-LC
6. customFractions were collected
7. temperatureFractions were pooled frozen

ORD record

ord-e3e2063839e24dceadcc58ac9c36def0

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278482B2