1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-{2-[2-(2-Methoxy-ethoxy)-ethoxy]-ethoxy}-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester

HRID 511772Notes

Reaction equation

HRID 511772 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].CCN=C=NCCCN(C)C.[CH3:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][CH2:33][C:34](O)=[O:35]>C(Cl)Cl>[O:8]=[C:3]1[CH2:4][CH2:5][C:6](=[O:7])[N:2]1[O:1][C:34](=[O:35])[CH2:33][CH2:32][CH2:31][O:30][CH2:29][CH2:28][O:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][O:21][CH3:20]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 57890900m-PEG4-(CH2)3-acid

Product 1

HCID 578909114-{2-[2-(2-Methoxy-ethoxy)-ethoxy]-ethoxy}-butyric acid 2,5-dioxo-pyrrolidin-1-yl esterYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

N-hydroxysuccinimide (0.55 g, 4.8 mmol) and EDCI (1.15 g, 6.0 mmol) were dissolved in CH2Cl2 (7 mL). Then 4-{2-[2-(2-Methoxy-ethoxy)-ethoxy]-ethoxy}-butyric acid (0.940 g, 3.8 mmol), dissolved in CH2Cl2 (2 mL), was added. Reaction stirred overnight at room temperature. Crude reaction was diluted with CH2Cl2 (21 mL), washed 1M HCl (30 mL), H2O (30 mL), dried MgSO4, and evaporated to dryness. Column chromatography (Silica, ethyl acetate) afforded 4, a clear oil (0.556 g, 43% yield).

Workup

  1. additionwas added
  2. customReaction
  3. customCrude reaction
  4. washwashed 1M HCl (30 mL), H2O (30 mL), dried MgSO4
  5. customevaporated to dryness
  6. customColumn chromatography (Silica, ethyl acetate) afforded 4

Sources & evidence

ORD record
ord-ca5488af8d4f493aaad90c58d005ddc5
Source dataset
uspto-grants-2015_08
Patent number
US09101596B2

Reaction notes

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