Pyridine → NHS-Biotin

HRID 1616993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616993
[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].C1(N=C=NC2CCCCC2)CCCCC1.N1C=CC=CC=1.O[N:39]1[C:43](=[O:44])[CH2:42][CH2:41][C:40]1=[O:45]>CN(C=O)C>[O:45]=[C:40]1[CH2:41][CH2:42][C:43](=[O:44])[N:39]1[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH:16]2[CH:11]([NH:12][C:13](=[O:14])[NH:15]2)[CH2:10][S:9]1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 171548Biotin

Produkt 1

HCID 434213NHS-BiotinAusbeute 83,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The method for synthesis of 2 was modified from that of Bayer and Wilchek. In brief, biotin (1; 0.31 g, 1.26 mmol) was completely dissolved in DMF (9 mL) with gentle warming. After cooling the 1 solution to room temperature without reprecipitation, it was added to N,N′-dicyclohexylcarbodiimide (DCC; 0.26 g, 1.28 mmol) and pyridine (0.10 mL, 1.26 mmol) while stirring for 5 min at room temperature, followed by the addition of N-hydroxysuccinimide (NHS; 0.19 g, 1.65 mmol) with continuous stirring for 24 h. The reaction product was filtered and concentrated under reduced pressure. The obtained solid was redissolved in 2-propanol (50 mL) with gentle heating, cooled down to room temperature, and reprecipitated at 4° C. overnight. The product was scraped out of the glassware, washed with cold 2-propanol, and air dried to give 2 as white solid (0.36 g; 82.4%). 1H NMR (400 MHz) (DMSO) δ: 6.46 (s, 1H, CONH), 6.39 (s, 1H, CONH), 4.31 (t, 1H, CHN), 4.16 (t, 1H, CHN), 3.12 (dd, 1H, CHS), 2.83 (s, 4H, CH2 of NHS), 2.71 (d, 1H, CHHS), 2.69 (t, 2H, CH2CO), 2.59 (d, 1H, CHHS), 1.43-1.68 (m, 6H). 13C NMR (100.67 MHz) (DMSO) δ: 170.42, 162.85, 61.01, 59.28, 55.33, 30.08, 27.91, 27.68, 25.51. HRMS (ESI) calculated for C14H19N3O5S, [M+Na]+ 364.0943 (calcd.), 364.0940 (found).

Aufarbeitung

  1. customThe method for synthesis of 2
  2. customwithout reprecipitation, it
  3. stirringwith continuous stirring for 24 h
  4. filtrationThe reaction product was filtered
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe obtained solid was redissolved in 2-propanol (50 mL) with gentle heating
  7. temperaturecooled down to room temperature
  8. customreprecipitated at 4° C. overnight
  9. washwashed with cold 2-propanol, and air
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6eba3bacb59e42d3a99d40ad7f55ca7c
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765934B2

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