Hydrochloric Acid → HCID 45117213, compound

Temperature

0 °C

The carboxylic acid of preparation 11 (18.26 g, 82.0 mmol) was dissolved in tetrahydrofuran (450 ml) and the solution cooled to 0° C. and treated dropwise with a solution of methylmagnesium chloride in tetrahydrofuran (82 ml, 246 mmol). The reaction mixture was allowed to warm to room temperature and left to stand for 18 hours. The reaction mixture was slowly diluted with water (80 ml) followed by 2M hydrochloric acid (120 ml, 240 mmol). The mixture was extracted with ethyl acetate (3×100 ml) and the organic extracts combined and washed with brine (3×50 ml). The ethyl acetate phase was dried (magnesium sulphate) and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:acetic acid (99.6:0:0.4 changing to 94.6:5:0.4) to yield the title product as a colourless solid.

1. temperatureto warm to room temperature
2. waitleft
3. extractionThe mixture was extracted with ethyl acetate (3×100 ml)
4. washwashed with brine (3×50 ml)
5. dry with materialThe ethyl acetate phase was dried (magnesium sulphate)
6. concentrationconcentrated in vacuo
7. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:acetic acid (99.6:0:0.4 changing to 94.6:5:0.4)

ORD record

ord-c5e852c8f39e4ea1bf0765ff823f50d3

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07351742B2