Triethylamine → Diethyl 2-(benzyloxycarbonylamino)malonate

HRID 1937655Notes

Reaction equation

HRID 1937655 reaction equation
[CH2:1]([O:8][C:9](N1C(=O)CCC1=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:19][CH:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:19][CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)HCID 3826287Benzyl 2,5-dioxopyrrolidine-1-carboxylate

Product 1

HCID 259787Diethyl 2-(benzyloxycarbonylamino)malonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

N-(Benzyloxycarbonyl)succinimide (5.6 g, 22.4 mmol) was dissolved in CH2Cl2 (25 mL) and the solution was added to a cooled (0° C.) and stirred solution of diethyl aminomalonate hydrochloride (5.0 g, 23.6 mmol) and triethylamine (13.4 mL, 95 mmol) in CH2Cl2 (125 ml). The resulting solution was stirred at 0° C. for 10 min and then at rt for 1 h. The solution was washed with 10% citric acid (2×50 mL),10% sodium hydrogen carbonate (2×50 mL), and water (50 mL) and was then dried (Na2SO4) and evaporated to afford diethyl N-benzyloxycarbonylaminomalonate as a colorless oil, which crystallized upon standing at 0° C. (6.3 g) (LC/Mass + ion): 310 (M+H).

Workup

  1. additionthe solution was added to
  2. waitat rt for 1 h
  3. washThe solution was washed with 10% citric acid (2×50 mL),10% sodium hydrogen carbonate (2×50 mL), and water (50 mL)
  4. dry with materialwas then dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-56a26b607c43499a90cf10c2e675a71a
Source dataset
uspto-grants-2002_05
Patent number
US06395767B2

Reaction notes

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