2-Nitrobenzenesulfonyl chloride → N-[(2S)-1-Hydroxypropan-2-yl]-2-nitrobenzene-1-sulfonamide

To a solution of (S)-(+)-2-amino-1-propanol (2.6 kg, 35 mol) in purified water (10.5 L) was added sodium bicarbonate (4.4 kg, 52 mol). To the resulting mixture was added a solution of 2-nitrobenzenesulfonyl chloride (7.3 kg, 33 mol) in tetrahydrofuran (10.2 L) at an internal temperature of −8° C. to −6° C. Subsequently, the resulting reaction mixture was stirred at room temperature for 39 hours. After confirming the disappearance of 2-nitrobenzenesulfonyl chloride by TLC, the mixture was filtered. The filtrate was then extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine, dried over magnesium sulfate, and filtered. The filtrate was then concentrated under reduced pressure. The residue thus obtained was crystallized from petroleum ether/ethyl acetate to give the target product as a white solid (7.5 kg, yield 82.4%).

1. customSubsequently, the resulting reaction mixture
2. filtrationthe mixture was filtered
3. extractionThe filtrate was then extracted with ethyl acetate
4. washthe resulting organic layer was washed with saturated brine
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was then concentrated under reduced pressure
8. customThe residue thus obtained
9. customwas crystallized from petroleum ether/ethyl acetate

ORD record

ord-cd830114578f46d7b9ea5c0d0b7ea8f3

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045460B2