Ethyl Acetate → N-Succinimidyl 4-(2-pyridyldithio)butanoate

HRID 895081Notes

Reaction equation

HRID 895081 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].O[N:16]1[C:20](=[O:21])[CH2:19][CH2:18][C:17]1=[O:22].CN(C)CCCN=C=NCC.C(OCC)(=O)C>ClCCl>[CH2:19]1[C:20](=[O:21])[N:16]([O:13][C:12]([CH2:11][CH2:10][CH2:9][S:8][S:7][C:2]2[N:1]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:14])[C:17](=[O:22])[CH2:18]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 11629990250266-79-6

Product 1

HCID 11551591N-Succinimidyl 4-(2-pyridyldithio)butanoateYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 11a (1.10 g, 4.8 mmol) and N-hydroxysuccinimide (0.64 g, 5.5 mmol) were dissolved in dichloromethane (50 mL). The solution was magnetically stirred as 1-[3-(dimethylamino)propyl]-3 ethylcarbodiimide (1.05 g, 5.5 mmol) was added. After 2 h, ethyl acetate (150 mL) was added and the solution was transferred to a separatory funnel and washed consecutively with 0.5 M HCl (30 mL) and saturated sodium chloride (20 mL). The organic layer was dried over anhydrous sodium sulfate, and then the solvent was removed under vacuum. The residue was taken up in a minimum volume of ethyl acetate and was purified by silica chromatography using a mobile phase of hexanes:ethyl acetate:acetic acid (2.5:1:0.02, v/v/v). Fractions containing pure product were combined and solvent was removed to give N-succinimidyl 4-(2-pyridyldithio)butanoate (SPDB, 3a) (1.2 g, 76% yield). 1H NMR (CDCl3): δ 2.12-2.19 (2H, m), 2.78-2.87 (6H, m), 2.91 (2H, t, J=7.0), 7.06-7.12 (1H, m), 7.62-7.71 (2H, m), 8.48 (1H, d, 4.4 Hz). MS (M+Na+) Found: 348.8 Calculated: 349.4.

Workup

  1. additionwas added
  2. customthe solution was transferred to a separatory funnel
  3. washwashed consecutively with 0.5 M HCl (30 mL) and saturated sodium chloride (20 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was removed under vacuum
  6. customwas purified by silica chromatography
  7. additionFractions containing pure product
  8. customsolvent was removed

Sources & evidence

ORD record
ord-7eaacde01dd44ca98713085a8abd352a
Source dataset
uspto-grants-2005_07
Patent number
US06913748B2

Reaction notes

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