Triethylamine → HCID 57989054, Verbindung

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.20 g) was added to a solution of 9-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-fluorobenzyl)-1-oxa-4,9-diazaspiro[5.5]undecane (example 78, step d) (0.17 g), 6-isopropylpicolinic acid (example 85, step d) (0.07 g) and triethylamine (0.22 mL) in DMF (7 mL) at 0° C. The resulting yellow solution was allowed to warm to RT and was stirred for 2 h. The mixture was partitioned between ethyl acetate (100 mL) and brine (100 mL). The organic phase was separated, washed with brine (2×100 mL), dried over sodium sulphate, filtered and the solvent evaporated. The residue was dissolved in THF (10 mL) and a solution of TBAF in THF (1M, 0.8 mL) was added. The resulting mixture was stirred for 2 h and the solvent evaporated. Purification was by silica gel chromatography eluting with 47.5:47.5:5 isohexane:ethyl acetate:triethylamine to 95:5 ethyl acetate:triethylamine gradient. The fractions containing product were combined, toluene (50 mL) was added and the solvent evaporated under reduced pressure to give the subtitled compound as a clear gum. Yield 0.2 g.

1. customThe mixture was partitioned between ethyl acetate (100 mL) and brine (100 mL)
2. customThe organic phase was separated
3. washwashed with brine (2×100 mL)
4. dry with materialdried over sodium sulphate
5. filtrationfiltered
6. customthe solvent evaporated
7. dissolutionThe residue was dissolved in THF (10 mL)
8. additiona solution of TBAF in THF (1M, 0.8 mL) was added
9. stirringThe resulting mixture was stirred for 2 h
10. customthe solvent evaporated
11. customPurification
12. washeluting with 47.5:47.5:5 isohexane
13. additionThe fractions containing product
14. additiontoluene (50 mL) was added
15. customthe solvent evaporated under reduced pressure

ORD-Eintrag

ord-7417c3cc21864545bd72927da5542819

Quelldatensatz

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08629271B2