Diisopropylethylamine → 1-tert-Butyl 18-(2,5-dioxopyrrolidin-1-yl) octadecanedioate

HRID 72096Notes

Reaction equation

HRID 72096 reaction equation
[C:1]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O-:20])=[O:19].CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(O[N:49]1[C:54](=[O:55])[CH2:53][CH2:52][C:50]1=[O:51])=[N+](C)C)C>C1COCC1>[C:18]([O:20][N:49]1[C:54](=[O:55])[CH2:53][CH2:52][C:50]1=[O:51])(=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 27282472Octadecanedioic acid, mono(1,1-dimethylethyl) ester

Product 1

HCID 582492131-tert-Butyl 18-(2,5-dioxopyrrolidin-1-yl) octadecanedioateYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of mono-tert-butyl octadecanedioate (1,00 g, 2.7 mmol) in dry THF (8 ml), was added DIPEA (0,555 ml, 3.2 mmol) followed by TSTU (1,00 g, 3.2 mmol). The reaction mixture was stirred under nitrogen for 18 h. The solvent had evaporated. AcOEt was added to the residue and the resulting suspension was filtered. The filtrate was washed with cold 0.1 M HCl (2×) and water, dried and concentrated to give succinimidyl tert-butyl octadecandioate as a white solid.

Workup

  1. customThe solvent had evaporated
  2. additionAcOEt was added to the residue
  3. filtrationthe resulting suspension was filtered
  4. washThe filtrate was washed with cold 0.1 M HCl (2×) and water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-16fecb24f7d54ed6b70f03642d1087c7
Source dataset
uspto-grants-2014_09
Patent number
US08828923B2

Reaction notes

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