Tetrahydrofuran → HCID 60023926, compound

Tetrahydrofuran (THF, 100 mL) and a 1.0M solution of vinyl magnesium bromide in THF (360 mL, 360 mmol, 3.1 equiv) was cooled to −78° C. while stirring under a nitrogen atmosphere. The mixture was treated dropwise with a solution of [(R)-(methoxy-methyl-carbamoyl)-methyl-propyl]-carbamic acid tert-butyl ester (30.3 g, 116 mmol, 1 equiv) in THF (50 mL) over 30 min. After the resultant dark yellow mixture was stirred for 30 min at −78° C., the cooling bath was removed and the reaction mixture was warmed slowly to room temperature overnight (15 h). The reaction mixture was poured slowly into an ice-chilled solution of 1N aqueous hydrochloric acid (700 mL) and then warmed to room temperature. The organics were extracted with (3×600 mL) ethyl acetate, dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by flash column chromatography (5-10% ethyl acetate/hexanes) provided the product as a white solid (16.8 g, 64%). ESMS [M+H]+: 228.4.

1. stirringAfter the resultant dark yellow mixture was stirred for 30 min at −78° C.
2. customthe cooling bath was removed
3. additionThe reaction mixture was poured slowly into an ice-
4. temperaturechilled solution of 1N aqueous hydrochloric acid (700 mL)
5. temperaturewarmed to room temperature
6. extractionThe organics were extracted with (3×600 mL) ethyl acetate
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customPurification by flash column chromatography (5-10% ethyl acetate/hexanes)

ORD record

ord-b7b8eb757fa146bf9eabb174ba4a9ede

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07629477B2