Acetic Acid → HCID 10171525, compound

Temperature

80 °C

Tetrabutylammonium fluoride trihydrate (252 mg, 0.80 mmol) and AcOH (0.057 mL, 1.0 mmol) are dissolved in tetrahydrofuran (4 mL) and this is used to dissolve the title A compound, N-(2-trimethylsilanyl-ethoxycarbonyl-aminosulfonyl)-N-(1H-indol-5ylmethyl)-glycine methyl ester (90 mg, 0.20 mmol) in a thick-walled round bottomed flask. This is sealed and stirred in an oil bath at 80° C. for 16 h. The reaction is allowed to cool, then diluted with 1N aqueous HCl (5 mL) and Et2O (25 mL). The organic layer is separated and washed with water (2×5 mL) and saturated aqueous NaCl (5 mL), then separated, dried over anhydrous MgSO4, filtered and evaporated, to yield the crude product as a brown oil. This is taken up in water (4.5 mL), MeCN (0.7 mL) and DMSO (1 mL). The resulting mixture is loaded onto a preparative reverse phase HPLC column (YMC CombiPrep Pro Cl 8, 50×20 mm I.D., particle size S-5 micron, 12 nM) in 3 aliquots and eluted at 30 mL/min with a gradient of 90:10 (water containing 0.1% TFA: MeCN) at 0 min to 10:90 at 5 min. Then held at 10:90 until 7 minutes. Fractions containing product are combined and concentrated on a Savant Speedvac to yield 5-(1H-indol-5-ylmethyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one as a light tan foam: [M−1]−=264.

1. customThis is sealed
2. temperatureto cool
3. customThe organic layer is separated
4. washwashed with water (2×5 mL) and saturated aqueous NaCl (5 mL)
5. customseparated
6. dry with materialdried over anhydrous MgSO4
7. filtrationfiltered
8. customevaporated
9. customto yield the crude product as a brown oil
10. washeluted at 30 mL/min with a gradient of 90:10 (water containing 0.1% TFA: MeCN) at 0 min to 10:90 at 5 min
11. waitThen held at 10:90 until 7 minutes
12. additionFractions containing product
13. concentrationconcentrated on a Savant Speedvac

ORD record

ord-de337bcc565045f483e8fe6184ac57cf

Source dataset

uspto-grants-2007_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07291635B2