Diglycolamine → HCID 123226547, compound

Temperature

75 °C

2-(2-Aminoethoxyl)ethanol (0.7 g, 5 eq.) was added to a solution of 2-[2-(tert-butoxycarbonylamino)ethoxy]ethyl 4-methylbenzenesulfonate (0.5 g, 1 eq.) in dry acetonitrile (10 mL) and the reaction mixture was heated to 75° C. for 3 h and then at 85° C. for 1 h. The acetonitrile was removed in vacuo. The crude residue was redissolved in DCM (25 mL) and washed with water (25 mL) the aqueous phase was re-extracted with DCM (2×25 mL). The combined organic phases were washed with water (50 mL), dried (MgSO4), filtered and concentrated at reduced pressure to a pale yellow oil (0.4 g). The crude product was purified by silica column chromatography eluting with 10% methanolic ammonia in DCM to give 0.19 g (50%) of 18 as a colourless oil. 13C NMR (CDCl3) δ 156.1, 72.5, 70.2, 70.1, 61.9, 49.2, 49.0, 40.5, 28.4. ESMS (C13H28N2O5) [M+H]+ calc. 293.2076. found 293.2076.

1. customThe acetonitrile was removed in vacuo
2. dissolutionThe crude residue was redissolved in DCM (25 mL)
3. washwashed with water (25 mL) the aqueous phase
4. extractionwas re-extracted with DCM (2×25 mL)
5. washThe combined organic phases were washed with water (50 mL)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated at reduced pressure to a pale yellow oil (0.4 g)
9. customThe crude product was purified by silica column chromatography
10. washeluting with 10% methanolic ammonia in DCM

ORD record

ord-50dc1ec7a14e457b9f86852cd1cc10a5

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359392B2