2-Mesitylenesulfonyl chloride → 3-tert-Butoxycarbonylamino-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid methyl ester

HRID 650668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 650668
[CH3:1][O:2][C:3](=[O:15])[CH:4]([NH2:14])[CH2:5][NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[C:16]1([CH3:28])[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[C:17]=1[S:24](Cl)(=[O:26])=[O:25].CCN(C(C)C)C(C)C>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:15])[CH:4]([NH:14][S:24]([C:17]1[C:18]([CH3:23])=[CH:19][C:20]([CH3:22])=[CH:21][C:16]=1[CH3:28])(=[O:26])=[O:25])[CH2:5][NH:6][C:7]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8]

Komponenten

6

Edukt 3

HCID 130462-Mesitylenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 3442239Methyl 2-amino-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate

Produkt 1

HCID 220066833-tert-Butoxycarbonylamino-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid methyl esterAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 3-tert-Butoxycarbonylamino-2-aminopropionic acid methyl ester (3.5 g, 13.7 mmol), mesitylsulfonyl chloride (3.9 g, 17.8 mmol), DIEA (7.2 mL, 41.1 mmol) in dichloromethane (100 mL) was stirred at 0° C. for one hour and overnight at room temperature. The solvent was removed and the crude reaction product was taken up in ethyl acetate (340 mL). The solution was washed with 5% solution of sodium carbonate (30 mL), 5% solution of hydrochloric acid (30 mL), with saturated sodium chloride solution (30 mL). Solvent was than dried over sodium sulfate and evaporated. Purification of the residue on silica gel (10%MeOH-EtOAc) gave 5.00 g of pure compound O-1 (84% yield).

Aufarbeitung

  1. customThe solvent was removed
  2. customthe crude reaction product
  3. washThe solution was washed with 5% solution of sodium carbonate (30 mL), 5% solution of hydrochloric acid (30 mL), with saturated sodium chloride solution (30 mL)
  4. dry with materialthan dried over sodium sulfate
  5. customevaporated
  6. customPurification of the residue on silica gel (10%MeOH-EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-1e9bfc59ac1f4141a3284f99a1723b56
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06274620B1

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