Methylamine → HCID 14860688, compound

HRID 2256000Notes

Reaction equation

HRID 2256000 reaction equation
[C:1]([NH:4][CH:5](Br)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].C[NH2:13].O1[CH2:18][CH2:17]CC1>>[CH3:17][CH2:18][NH:13][CH:5]([NH:4][C:1]([CH3:2])=[O:3])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 8028Tetrahydrofuran2×HCID 13082363HCID 13082363, compound

Product 1

HCID 14860688HCID 14860688, compound

Conditions

Temperature
-78 °C

Procedure

A cold (-78° C.) solution of ethyl 2-acetamido-2-bromoacetate (2.10 g, 9.38 mmol) in dry tetrahydrofuran (80 mL) was added slowly into a cooled (-78° C.) tetrahydrofuran (20 mL) solution of methylamine (1.40 g, 31.04 mmol) over a period of 20 min. The reaction was stirred at -78° C. (1 h), and then at room temperature (1 h). The precipitated salt was filtered and the filtrate concentrated. The residue was purified by flash column chromatography on SiO2 using 3% methanol/chloroform as the eluent to yield the desired compound as a light yellow oil.

Workup

  1. customat room temperature
  2. custom(1 h)
  3. filtrationThe precipitated salt was filtered
  4. concentrationthe filtrate concentrated
  5. customThe residue was purified by flash column chromatography on SiO2 using 3% methanol/chloroform as the eluent

Sources & evidence

ORD record
ord-3c72009f7b564155bd7ffa527a7c6ca7
Source dataset
uspto-grants-1997_08
Patent number
US05654301

Reaction notes

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