1,1'-Carbonyldiimidazole → n-Hydroxysuccinimide biotin

HRID 1761838

반응식

HRID 1761838 반응식
[OH:1][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:3].C1N=CN(C(N2C=NC=C2)=O)C=1.[OH:29][N:30]1[C:34](=[O:35])[CH2:33][CH2:32][C:31]1=[O:36]>CN(C=O)C>[OH:29][N:30]1[C:34](=[O:35])[CH2:33][CH2:32][C:31]1=[O:36].[OH:3][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:1]

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 80170N-HydroxysuccinimideHCID 171548Biotin

생성물 1

HCID 86743017n-Hydroxysuccinimide biotin수율 61%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

Biotin (1.0 g, 4.1 mmole) was dissolved in 10 ml DMF (dry) with heating at 80° C. in oil bath. CDI (665 mg, 4.1 mmoles) was added and the mixture was heated at 80° C. The reaction mixture was stirred at 80° C. for 30 minutes, then at room temperature for 2 hours; a white precipitate formed. N-hydroxysuccinimide (475 mg, 4.1 mmoles) was added and the reaction mixture was stirred at room temperature overnight. DMF was removed under vacuum on rotary evaporator. The solid residue was dissolved in 250 ml of refluxing isopropanol, filtered, and stored in the cold room overnight. The precipitate was filtered, washed one time with cold isopropanol and dried in vacuo at 45° C. overnight to give 870 mg (61% yield) of the desired product.

후처리

  1. temperaturethe mixture was heated at 80° C
  2. waitat room temperature for 2 hours
  3. customa white precipitate formed
  4. stirringthe reaction mixture was stirred at room temperature overnight
  5. customDMF was removed under vacuum on rotary evaporator
  6. dissolutionThe solid residue was dissolved in 250 ml of refluxing isopropanol
  7. filtrationfiltered
  8. customstored in the cold room overnight
  9. filtrationThe precipitate was filtered
  10. washwashed one time with cold isopropanol
  11. customdried in vacuo at 45° C. overnight

출처 및 근거

ORD 기록
ord-4f78a3a76fa14516a708c8c9afd5f6bd
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04828979

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