Triethylamine → Ethyl (cyclopropylamino)(oxo)acetate

HRID 2272688Notes

Reaction equation

HRID 2272688 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>O1CCCC1>[CH2:17]([O:16][C:14](=[O:15])[C:13]([NH:4][CH:1]1[CH2:3][CH2:2]1)=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 69828Cyclopropylamine

Product 1

HCID 28710173Ethyl (cyclopropylamino)(oxo)acetateYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of cyclopropylamine (1.39 g, 24.3 mmol) and triethylamine (3.5 g, 35 mmol) was added drop-wise to a 0° C. solution of ethyl chloro(oxo)acetate (3.5 g, 26 mmol) in tetrahydrofuran (25 mL). The reaction mixture was stirred at 0° C. for 10 minutes and filtered; the filtrate was concentrated in vacuo to afford the product as a yellow solid Yield: 3.0 g, 19 mmol, 78%. 1H NMR (400 MHz, CDCl3) δ 7.14 (br s, 1H), 4.34 (q, J=7.2 Hz, 2H), 2.78-2.86 (m, 1H), 1.38 (t, J=7.2 Hz, 3H), 0.83-0.90 (m, 2H), 0.59-0.65 (m, 2H).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e759179bd1414e6b85a7c3ad95885057
Source dataset
uspto-grants-2015_09
Patent number
US09120788B2

Reaction notes

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