Water → HCID 14842658, compound

To a solution of Boc-Pro(4-cis-OH)-OBn (8.45 g, 26.3 mmol) in pyridine (65 mL) at 0° C., was added methanesulfonyl chloride (3.4 mL, 44 mmol) dropwise over 7 min. The reaction mixture was allowed to warm to room temperature over 2 h, then stirred overnight. A solution of 10% water in pyridine (20 mL) was added over 15 min and the reaction mixture was concentrated. The residue was dissolved in water and extracted with ethyl acetate (2×200 mL). The combined organic layers were washed with water (2×50 mL) saturated aqueous sodium bicarbonate (50 mL) and saturated aqueous sodium chloride (50 mL), dried (sodium sulfate), filtered and concentrated. The resulting residue was dissolved in toluene (100 mL) and concentrated to remove traces of pyridine. The residue was dried in vacuo for 30 min to afford the title compound (10.7 g, 102%), then used in the next step without purification.

1. concentrationthe reaction mixture was concentrated
2. dissolutionThe residue was dissolved in water
3. extractionextracted with ethyl acetate (2×200 mL)
4. washThe combined organic layers were washed with water (2×50 mL) saturated aqueous sodium bicarbonate (50 mL) and saturated aqueous sodium chloride (50 mL)
5. dry with materialdried (sodium sulfate)
6. filtrationfiltered
7. concentrationconcentrated
8. dissolutionThe resulting residue was dissolved in toluene (100 mL)
9. concentrationconcentrated
10. customto remove traces of pyridine
11. customThe residue was dried in vacuo for 30 min

ORD record

ord-41834fe684d44aa48e454fba91bfdd8b

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592316B2