Ethanolamine → 2,5-Dimethylhexane-2,5-diyl bis(2-(2-hydroxyethylamino)acetate)

HRID 340858Notes

Reaction equation

Cl[CH2:2][C:3]([O:5][C:6]([CH3:18])([CH2:8][CH2:9][C:10]([O:13][C:14](=[O:17])[CH2:15]Cl)([CH3:12])[CH3:11])[CH3:7])=[O:4].[CH2:19]([CH2:21][NH2:22])[OH:20]>C(Cl)Cl>[OH:20][CH2:19][CH2:21][NH:22][CH2:2][C:3]([O:5][C:6]([CH3:18])([CH2:8][CH2:9][C:10]([O:13][C:14](=[O:17])[CH2:15][NH:22][CH2:21][CH2:19][OH:20])([CH3:12])[CH3:11])[CH3:7])=[O:4]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of compound (61) (0.898 g, 3 mmol) in 5 mL of methylene chloride at 0° C., ethanolamine (40) (2.504 g, 41 mmol) was added drop wise over the course of one hour. The solution was then allowed to warm to 20° C. and stirred for 18 hours. On completion, the reaction was diluted with CH2Cl2 (15 mL) and washed with brine (1×20 mL) and dried. The solvent was evaporated to get clear yellow oil. (0.380 g) 1H NMR (400 MHz, CDCl3): δ 1.35 (s, 12H), 1.79 (s, 4H), 2.68-2.71 (t, J=5.1, 4H), 3.08 (b, 4H), 3.26 (s, 4H), 3.58-3.60 (t, J=5.1, 4H).

Workup

washwashed with brine (1×20 mL)
customdried
customThe solvent was evaporated
customto get clear yellow oil

Sources & evidence

ORD record: ord-140b344d76124393afe04e6b8e919d76
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895691B2

Reaction notes

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