Diisopropylethylamine → Methyl succinimidyl hexadecandioate

HRID 72094Notes

Reaction equation

HRID 72094 reaction equation
[C:1]([O:20][CH3:21])(=[O:19])[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][C:16]([O-:18])=[O:17].F[B-](F)(F)F.[C:27]1(=[O:41])[N:31](OC(N(C)C)=[N+](C)C)[C:30](=[O:40])[CH2:29][CH2:28]1.C(N(CC)C(C)C)(C)C>C1COCC1>[C:1]([O:20][CH3:21])(=[O:19])[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][C:16]([O:18][N:31]1[C:27](=[O:41])[CH2:28][CH2:29][C:30]1=[O:40])=[O:17]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 85704850Hexadecanedioic acid, monomethyl ester

Product 1

HCID 86607066Methyl succinimidyl hexadecandioateYield 96.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Mono-methyl hexadecandioate (275 mg, 0.91 mmol) was dissolved in THF (3 ml) and treated with succinimidyl tetramethyluroniumtetrafluoroborate (331 mg, 1.1 mmol) and N,N-diisopropylethylamine (188 μL, 1.1 mmol), and the mixture was stirred for 20 hours. The solvent was removed in vacuo, and the residue was dissolved in ethyl acetate and washed with 0.1 M HCl (twice) and water. The organic phase was dried over MgSO4, filtered and evaporated in vacuo to give 350 mg (96%) of methyl succinimidyl hexadecandioate.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with 0.1 M HCl (twice) and water
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-85dd371f7e064da39140e3d6f053ce27
Source dataset
uspto-grants-2014_09
Patent number
US08828923B2

Reaction notes

Loading…