1-Hydroxybenzotriazole → HCID 66881268, compound

N-(tert-butoxycarbonyl)glycine (5.00 g, 28.5 mmol) and D-prolinol (3.50 g, 34.2 mmol) was dissolved in N,N-dimethylformamide (10 ml) and dichloromethane (100 ml), and the mixture was stirred at room temperature. At the same temperature, 1-hydroxybenzotriazole.monohydrate (7.70 g, 57.0 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (hereinafter to be indicated as WSC) (8.20 g, 42.8 mmol) were added, and the mixture was stirred at room temperature overnight. The reaction mixture was washed with diluted hydrochloric acid, diluted aqueous sodium hydroxide solution, water and saturated brine, and the organic layer was dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure, the obtained oil was purified by silica gel column chromatography (methanol-chloroform) to give a crude product. This was dissolved in ethyl acetate (30 ml) and methanol (20 ml), 4N hydrochloric acid-ethyl acetate solution (20 ml) was added, and the mixture was stirred at room temperature overnight. The solution was concentrated under reduced pressure, and to the obtained concentrate was added a saturated aqueous potassium carbonate solution, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the solution was concentrated under reduced pressure to give the title compound (1.00 g, yield 22%) as a pale-yellow oil.

1. washThe reaction mixture was washed with diluted hydrochloric acid, diluted aqueous sodium hydroxide solution, water and saturated brine
2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
3. filtrationThe insoluble material was filtered off
4. concentrationthe solution was concentrated under reduced pressure
5. customthe obtained oil was purified by silica gel column chromatography (methanol-chloroform)
6. customto give a crude product
7. stirringthe mixture was stirred at room temperature overnight
8. concentrationThe solution was concentrated under reduced pressure
9. concentrationto the obtained concentrate
10. additionwas added a saturated aqueous potassium carbonate solution
11. extractionthe mixture was extracted with chloroform
12. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
13. filtrationthe insoluble material was filtered off
14. concentrationthe solution was concentrated under reduced pressure

ORD record

ord-9ddd2f59e43142eab5821843de238fbc

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513235B2