Methylamine → Methylamino-PEG3-t-butyl ester

HRID 926796Notes

Reaction equation

HRID 926796 reaction equation
S(O[CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(C1C=CC(C)=CC=1)(=O)=O.[CH3:30][NH2:31]>O1CCCC1>[CH3:30][NH:31][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 60146205Tos-PEG4-t-butyl ester

Product 1

HCID 53662991Methylamino-PEG3-t-butyl esterYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Into a 250-mL sealed bottle was placed a solution of tert-butyl 3-(2-(2-(2-(tosyloxy)ethoxy)ethoxy)ethoxy)propanoate (14 g, 32.41 mmol, 1.00 equiv) in tetrahydrofuran (5 mL) followed by CH3NH2 (66.9 g, 712.16 mmol, 21.98 equiv, 33% in ethanol) and the resulting solution was stirred overnight at 50° C. The resulting mixture was concentrated under vacuum, dissolved in 150 mL of dichloromethane and then washed with 2×150 mL of water and 1×150 mL of brine. The organic layer was dried over sodium sulfate and concentrated under vacuum to afford 8.2 g (87%) of tert-butyl 3-(2-(2-(2-(methylamino)ethoxy)ethoxy)ethoxy)propanoate as yellow oil.

Workup

  1. customInto a 250-mL sealed bottle
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. dissolutiondissolved in 150 mL of dichloromethane
  4. washwashed with 2×150 mL of water and 1×150 mL of brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-fbe1e532b2b946e6b3c0adfa813ef738
Source dataset
uspto-grants-2016_03
Patent number
US09289429B2

Reaction notes

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