4-Tert-butyl 3-methyl 1,1-dioxo-1lambda6-thiomorpholine-3,4-dicarboxylate → 3-Thiomorpholinecarboxylic acid, methyl ester, 1,1-dioxide

HRID 2245401Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2245401
[N:1]1(C(OC(C)(C)C)=O)[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH:2]1[C:9]([O:11][CH3:12])=[O:10]>C(Cl)Cl.FC(F)(F)C(O)=O>[NH:1]1[CH2:6][CH2:5][S:4](=[O:7])(=[O:8])[CH2:3][CH:2]1[C:9]([O:11][CH3:12])=[O:10]

Komponenten

4

Edukt 1

HCID 592159004-Tert-butyl 3-methyl 1,1-dioxo-1lambda6-thiomorpholine-3,4-dicarboxylate

Produkt 1

HCID 592157783-Thiomorpholinecarboxylic acid, methyl ester, 1,1-dioxideAusbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 4-(1,1-dimethylethyl) 3-methyl 3,4-thiomorpholinedicarboxylate 1,1-dioxide (D15; 1.73 g, 5.9 mmol) in 17 ml of anhydrous methylene chloride, trifluoroacetic acid (4.2 ml) was added dropwise while stirring at 0° C. under nitrogen atmosphere. The solution was stirred for 3 h, while allowing it to reach room temperature. The solvent was removed under reduced pressure and the residue was loaded on a SCX cartridge, washed with methanol and eluted with 0.5M methanolic ammonia. The basic fractions were collected and the solvent removed leaving 1.08 g of the target product.

Aufarbeitung

  1. stirringThe solution was stirred for 3 h
  2. customto reach room temperature
  3. customThe solvent was removed under reduced pressure
  4. washwashed with methanol
  5. washeluted with 0.5M methanolic ammonia
  6. customThe basic fractions were collected
  7. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-cd4b59db7d3240348a88dca1ea534a67
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07683056B2

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