Reaktion #617721

Reaktionsgleichung

D-threonine

NaHCO3

2-pyridyl-[4-(3-thienyl)-phenyl]-methyl carbonate

[4-(3-thienyl)-phenyl]-methyl-2-oxopyridine-1-carboxylate

→

title compound

(2R,3S)-3-hydroxy-2-[[4-(3-thienyl)-phenyl]-methoxy-carbonylamino]-butanoic acid

Lösungsmittel

H2O

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Sonstigethe crude mixture was rotary evaporated
3. 3
   Sonstigeto remove the organics and
4. 4
   Extraktionsubsequently extracted with Et2O (3×5 mL)
5. 5
   Extraktionsubsequently extracted with EtOAc (3×10 mL)
6. 6
   TrocknenThe organic fraction was dried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated to dryness

Vorschrift

To a stirred mixture of D-threonine (0.067 g, 0.56 mmol) and NaHCO3 (0.07 g, 0.84 mmol) in H2O (3.0 mL), the crude mixture containing 2-pyridyl-[4-(3-thienyl)-phenyl]-methyl carbonate and [4-(3-thienyl)-phenyl]-methyl-2-oxopyridine-1-carboxylate (0.263 g, 0.84 mmol) in THF (3.0 mL) was added. After 15 h at rt, the crude mixture was rotary evaporated to remove the organics and subsequently extracted with Et2O (3×5 mL). The aqueous phase was acidified with 2.0 M HCl solution to pH 2-3 and subsequently extracted with EtOAc (3×10 mL). The organic fraction was dried over Na2SO4, filtered and concentrated to dryness to afford the title compound (0.188 g, quant.) as white solid, which was used in the next step without further purification. MS (ESI) m/z: 353 [M−NH4]+. 1H NMR (DMSO-d6) δ: 1.10 (d, J=6.4 Hz, 3H), 3.97 (dd, J=3.5, 8.9 Hz, 1H), 4.08 (dq, J=3.5, 6.4 Hz, 1H), 5.07 (s, 2H), 6.96 (d, J=8.9 Hz, 1H), 7.41 (d, J=8.1 Hz, 2H), 7.53-7.60 (m, 1H), 7.64 (dd, J=2.9, 5.0 Hz, 1H), 7.72 (d, J=8.1 Hz, 2H), 7.86-7.91 (m, 1H), 12.58 (s, 1H).

Quelle