반응 #1592499

반응 방정식

N-{[(1,1-dimethylethyl)oxy]carbonyl}-D-alanine

N,N-Dimethylformamide

TBTU

4-{[4-methyl-3-(methyloxy)phenyl]oxy}aniline

Intermediate 20

4-{[4-methyl-3-(methyloxy)phenyl]oxy}aniline

→

title compound

수율 87.0%

1,1-dimethylethyl {(1R)-1-methyl-2-[(4-{[4-methyl-3-(methyloxy)phenyl]oxy}phenyl)amino]-2-oxoethyl}carbamate

수율 87.0%

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction mixture was stirred for 1 hour at the same temperature
2. 2
   기타The reaction was quenched with water (2 mL)
3. 3
   workup.ADDITIONdiluted with brine (10 mL)
4. 4
   추출extracted with ethyl acetate (2 times 20 mL)
5. 5
   건조Organic layer was dried over sodium sulphate
6. 6
   여과filtered
7. 7
   기타evaporated
8. 8
   기타the residue was purified by flash chromatography (Biotage system, 10 g SNAP column)

실험 절차

To a solution of N-{[(1,1-dimethylethyl)oxy]carbonyl}-D-alanine (182 mg, 0.960 mmol) in dry N,N-Dimethylformamide (DMF) (4 mL) DIPEA (0.305 mL, 1.745 mmol) and then TBTU (336 mg, 1.047 mmol) were added and the reaction mixture was stirred for 15 minutes at r.t. 4-{[4-methyl-3-(methyloxy)phenyl]oxy}aniline (Intermediate 20, 200 mg) was then added and the reaction mixture was stirred for 1 hour at the same temperature. The reaction was quenched with water (2 mL), diluted with brine (10 mL) and extracted with ethyl acetate (2 times 20 mL). Organic layer was dried over sodium sulphate, filtered and evaporated and the residue was purified by flash chromatography (Biotage system, 10 g SNAP column) using as eluent a gradient cyclohexane/ethyl acetate from 100/0 to 80/20 to afford the title compound as a yellow pale solid (304 mg).

출처