1,2-Dichloroethane → 2,5-Dioxopyrrolidin-1-yl 2-(tert-butoxycarbonyl(methyl)amino)-2-methylpropanoate

HRID 1036692Notes

Reaction equation

HRID 1036692 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:15])[C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].ON[C:18](=[O:24])[CH2:19][CH2:20][C:21]([NH2:23])=[O:22].C(N(CC)CC)C.C(Cl)CCl>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([CH3:15])[C:9]([CH3:14])([CH3:13])[C:10]([O:12][N:23]1[C:21](=[O:22])[CH2:20][CH2:19][C:18]1=[O:24])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 27347522-{[(Tert-butoxy)carbonyl](methyl)amino}-2-methylpropanoic acidHCID 18381240N-hydroxysuccinamide

Product 1

HCID 866740982,5-Dioxopyrrolidin-1-yl 2-(tert-butoxycarbonyl(methyl)amino)-2-methylpropanoateYield 80.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(tert-butoxycarbonyl(methyl)amino)-2-methylpropanoic acid (5 g), N-hydroxysuccinamide (2.65 g) in DCM (100 mL) was added triethylamine (6.42 mL) and EDC (4.41 g). The reaction mixture was stirred at room temperature overnight. The reaction mixture was washed with sodium bicarbonate (100 mL), dried with magnesium sulfate, filtered and then concentrated to afford 2,5-dioxopyrrolidin-1-yl 2-(tert-butoxycarbonyl(methyl)amino)-2-methylpropanoate as a colourless oil (5.1 g).

Workup

  1. washThe reaction mixture was washed with sodium bicarbonate (100 mL)
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-de4727ac4ef74027aaaa6d9f3de515d5
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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