Dimethylformamide → O-{[(3-sulfophenyl)amino]carbonyl}-L-serine

HRID 705449Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 705449
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:5]([O:7]C(C)(C)C)=[O:6])[CH2:3][OH:4].N[C:20]1[CH:21]=[C:22]([S:26]([OH:29])(=[O:28])=[O:27])C=CC=1.CN(C=[O:34])C.C([N:38]([CH:41]([CH3:43])[CH3:42])[CH2:39]C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[S:26]([C:22]1[CH:43]=[C:41]([NH:38][C:39]([O:4][CH2:3][C@@H:2]([C:5]([OH:7])=[O:6])[NH2:1])=[O:34])[CH:42]=[CH:20][CH:21]=1)([OH:29])(=[O:28])=[O:27]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 84743-Aminobenzenesulfonic acidHCID 81531DiisopropylethylamineHCID 7019054Boc-Ser-Otbu

Produkt 1

HCID 45275682O-{[(3-sulfophenyl)amino]carbonyl}-L-serineAusbeute 0,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Boc-Ser-OtBu (200 mg, 0.77 mmol) was dissolved in 3 mL of methylene chloride and cooled down to 0° C. N,N′-carbonyldiimidazole (124 mg, 0.77 mmol) was added thereto and stirred at room temperature for 2 hours. After removing a solvent, 3-aminobenzenesulfonic acid (132.6 mg, 0.77 mmol), 2 mL of DMF and 0.4 mL of diisopropylethylamine were added thereto and stirred at 70° C. overnight. After removing a solvent, the mixture was purified in accordance with the purification process A to obtain an intermediate. The obtained intermediate was dissolved in 1 mL of TFA and stirred at room temperature for 2 hours. After removing a solvent, purification was conducted in accordance with the purification process A to obtain a title compound.

Aufarbeitung

  1. additionwere added
  2. stirringstirred at 70° C. overnight
  3. customAfter removing a solvent
  4. customthe mixture was purified in accordance with the purification process
  5. customA to obtain an intermediate
  6. stirringstirred at room temperature for 2 hours
  7. customAfter removing
  8. customa solvent, purification

Quellen und Nachweise

ORD-Eintrag
ord-acb1354df1474281a1e3ac071f222f3f
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174932B2

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