Ethyl bromoacetate → Ethyl N-(2-((tert-butoxycarbonyl)amino)ethyl)-N-methylglycinate

HRID 1777941Notes

Reaction equation

HRID 1777941 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:8]([O:12][C:13](=[O:19])[NH:14][CH2:15][CH2:16][NH:17][CH3:18])([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C>C1COCC1>[C:8]([O:12][C:13]([NH:14][CH2:15][CH2:16][N:17]([CH3:18])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:19])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 3435744N-(tert-Butoxycarbonyl)-N'-methylethylenediamine

Product 1

HCID 87241117Ethyl N-(2-((tert-butoxycarbonyl)amino)ethyl)-N-methylglycinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl bromoacetate (1.27 ml, 11.48 mmol) was added to a mixture of tert-butyl(2-(methylamino)ethyl)carbamate (2.0 g, 11.48 mmol), triethylamine (4.81 ml) and THF (24 ml) at 0° C. After stirring 24 h at room temperature the reaction mixture was partitioned between saturated aqueous NaHCO3 and DCM, extracted 2× with DCM, the organic layers dried over Na2SO4 and evaporated to give the title compound as a clear pale-yellow oil. 1H NMR (400 MHz, CDCl3) δ 5.20 (s, br, 1H), 4.18 (q, 2H), 3.24 (s, 2H), 3.22-3.16 (m, 2H), 2.65-2.61 (m, 2H), 2.38 (s, 3H), 1.42 (s, 9H), 1.24 (t, 3H).

Workup

  1. customwas partitioned between saturated aqueous NaHCO3 and DCM
  2. extractionextracted 2× with DCM
  3. dry with materialthe organic layers dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-c6a86e947d004805ba8ebafd7ba250c4
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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