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

HRID 895081노트

반응식

HRID 895081 반응식
[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

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 116299904-(2-Pyridyldithio)butanoic acid

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7eaacde01dd44ca98713085a8abd352a
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06913748B2

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