N-Hydroxysuccinimide → HCID 69746761, compound

HRID 1530862Notes

Reaction equation

HRID 1530862 reaction equation
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].O[N:22]1[C:26](=[O:27])[CH2:25][CH2:24][C:23]1=[O:28]>C1COCC1>[C:23]1(=[O:28])[NH:22][C:26](=[O:27])[CH2:25][CH2:24]1.[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 80170N-HydroxysuccinimideHCID 445639Oleic Acid

Product 1

HCID 69746761HCID 69746761, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dicyclcohexylcarbodiimide (24.1 g, 117 mmol) dissolved in THF is added to a solution of oleic acid (30 g, 106.2 mmol) in 150 ml of THF at 0° C. After 20 minutes, N-hydroxysuccinimide (13.5 g, 117 mmol) is added to the mixture. The mixture is slowly warmed to room temperature. After 18 hours at room temperature, cooling to 0° C. is effected, and the precipitate is sucked off. The filtrate is concentrated and purified on a silica gel column using ethyl acetate/heptene (1:3). Yield: 83% of a colorless wax.

Workup

  1. waitAfter 18 hours at room temperature
  2. temperaturecooling to 0° C.
  3. concentrationThe filtrate is concentrated
  4. custompurified on a silica gel column

Sources & evidence

ORD record
ord-91edad3179ac448dbde8f3624b980d2e
Source dataset
uspto-grants-2001_03
Patent number
US06197759B1

Reaction notes

Loading…