Ethyl bromoacetate → Ethyl N-{2-[(tert-butoxycarbonyl)amino]ethyl}glycinate

HRID 1777977Notes

Reaction equation

HRID 1777977 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:8]([O:12][C:13](=[O:18])[NH:14][CH2:15][CH2:16][NH2:17])([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C>C1COCC1>[C:8]([O:12][C:13]([NH:14][CH2:15][CH2:16][NH:17][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:18])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 187201N-BOC-ethylenediamine

Product 1

HCID 4319362Ethyl N-{2-[(tert-butoxycarbonyl)amino]ethyl}glycinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl bromoacetate (10.35 ml, 94.0 mmol) was added drop wise to a mixture of tert-butyl(2-aminoethyl)carbamate (15.0 g, 94.0 mmol), triethylamine (16.87 ml, 122 mmol) and THF (200 ml) at 0° C. After stirring 18 h at room temperature the reaction mixture was filtered, the filtrate diluted with DCM, washed with water, the organic layer dried over Na2SO4 and evaporated to give the title compound as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 6.62 (s, br, 1H), 4.00 (q, 2H), 3.28 (s, 2H), 3.04-2.90 (m, 2H), 2.58-2.49 (m, 2H), 1.26 (s, 9H), 1.11 (t, 3H).

Workup

  1. filtrationwas filtered
  2. additionthe filtrate diluted with DCM
  3. washwashed with water
  4. dry with materialthe organic layer dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-ca480a8943c24f9b82bd7c4a00e2e7da
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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