Diisopropylcarbodiimide → HCID 86704391, Verbindung

HRID 1408300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1408300
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][C:26]([OH:28])=[O:27])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.O[N:30]1[C:34](=[O:35])[CH2:33][CH2:32][C:31]1=[O:36].CC(C)N=C=NC(C)C>C1COCC1>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][C:26]([O:28][N:30]3[C:34](=[O:35])[CH2:33][CH2:32][C:31]3=[O:36])=[O:27])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 12734DiisopropylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 27560922-(2-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)ethoxy)ethoxy)acetic acid

Produkt 1

HCID 86704391HCID 86704391, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-[2-(2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethoxy)ethoxy]acetic acid (185 mg, 0.480 mmol) and N-hydroxysuccinimide (110 mg, 0.956 mmol) were dissolved in anhydrous THF (1.5 mL). DIC was added dropwise to the solution at r.t., leading to the precipitation of a white solid. After 2 h, the reaction mixture was filtrated through a PTFE membrane filter (0.2 μm), and the solvent was removed. The crude product was redissolved in Et2O. The organic phase was washed with aq. NaHCO3 and 0.5 M aq. HCl. The organic layer was dried over Na2SO4, and the solvent was removed. The crude product was dissolved in CH2Cl2, and the solution was filtrated. After removal of the solvent, the crude product 39 (210 mg) was used in the synthesis of 40 without further purification.

Aufarbeitung

  1. customleading to the precipitation of a white solid
  2. filtrationthe reaction mixture was filtrated through a PTFE membrane
  3. filtrationfilter (0.2 μm)
  4. customthe solvent was removed
  5. dissolutionThe crude product was redissolved in Et2O
  6. washThe organic phase was washed with aq. NaHCO3 and 0.5 M aq. HCl
  7. dry with materialThe organic layer was dried over Na2SO4
  8. customthe solvent was removed
  9. dissolutionThe crude product was dissolved in CH2Cl2
  10. filtrationthe solution was filtrated
  11. customAfter removal of the solvent
  12. customthe crude product 39 (210 mg) was used in the synthesis of 40 without further purification

Quellen und Nachweise

ORD-Eintrag
ord-d5d8c9c9c6c941a99efc6218c7e2607b
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921328B2

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