O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → 2-{[(2R)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino}ethane-1-sulfonic acid

HRID 1765334

Reaktionsgleichung

Reaktionsgleichung von HRID 1765334
C(N([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)CC(O)=O)(OC(C)(C)C)=O.[NH2:20][CH2:21][CH2:22][S:23]([OH:26])(=[O:25])=[O:24].[CH2:27]([N+:31](CCCC)(CCCC)CCCC)[CH2:28]CC.CN(C([O:51]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[NH2:31][C@H:27]([C:13]1[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=1)[C:28]([NH:20][CH2:21][CH2:22][S:23]([OH:26])(=[O:25])=[O:24])=[O:51]

Komponenten

5

Edukt 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21896665Tetrabutylammonium taurineHCID 21896684N-Boc-p-hydroxyphenylglycine

Produkt 1

HCID 713630852-{[(2R)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino}ethane-1-sulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

N-Boc-4-hydroxyphenylglycine (1.00 g, 3.21 mmol) was dissolved in DMF (5 ml) and tetrabutylammonium taurine (2.36 g, 6.42 mmol) was added together with additionally 5 ml DMF. The resulting suspension was cooled on ice and TBTU (1.24 g, 3.85 mmol) was added. The ice bath was removed after 30 min and the mixture was stirred for 2 hours before it was filtered and concentrated. TFA in DCM (20%, 20 ml) was added and the reaction mixture was stirred over night. Ethanol (20 ml) was added and the solvents evaporated. The crude product was refluxed in ethanol (100 ml) for 1 hour. Filtration yielded the pure title compound as a white solid, 626 mg (71%). NMR DMSO-d6): 2.4–2.6 (m, 2H),3.2–3.4 (m, 2H),4.79 (s, 1H), 6.78 (d, 2H), 7.23 (d, 2H), 8.22 (t, 1H), 8.4 (brs, 3H), 9.7 (s, 1H).

Aufarbeitung

  1. additionwas added
  2. customThe ice bath was removed after 30 min
  3. filtrationwas filtered
  4. concentrationconcentrated
  5. additionTFA in DCM (20%, 20 ml) was added
  6. stirringthe reaction mixture was stirred over night
  7. additionEthanol (20 ml) was added
  8. customthe solvents evaporated
  9. temperatureThe crude product was refluxed in ethanol (100 ml) for 1 hour
  10. filtrationFiltration

Quellen und Nachweise

ORD-Eintrag
ord-dd0441e2f89c4612b064616c35b4eae4
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07226943B2

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