Carbon Dioxide → Alanine benzyl ester isocyanate

HRID 2082591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2082591
[C:1](=[O:3])=O.Cl.[CH2:5]([O:12][C:13](=[O:17])[C@H:14]([CH3:16])[NH2:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.P(Cl)(Cl)(Cl)=O>ClCCl.C(OCC)C>[N-:15]=[C:1]=[O:3].[CH2:5]([O:12][C:13](=[O:17])[C@H:14]([CH3:16])[NH2:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

7

Edukt 4

HCID 280Carbon Dioxide2×HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 12210893L-Alanine, phenylmethyl ester, hydrochloride (1:1)

Produkt 1

HCID 86746569Alanine benzyl ester isocyanate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Carbon dioxide was added subsurface to a dichloromethane (20 mL) solution containing alanine benzyl ester hydrochloride salt (0.003 mol, 0.65 g) and triethylamine (0.013 mol, 1.3 g) at -10° C. (ice and salt bath) for 30 min at a pressure of psig. The reaction mixture was transferred via cannula all at once under carbon dioxide to the precooled solution of phosphorus oxychloride (0.003 mol, 0.5 g) in 20 mL dichloromethane. After stirring for 20 min at -10° C. diethylether (40 mL) was added to the reaction mixture. A white ppt formed and was filtered off. The filtrate was concentrated in vacuo and the residue was extracted with 3×20 mL diethylether. The ether layers were concentrated and the residue was distilled under vacuum (ca. 0.1-0.3 torr) collecting product, alanine benzyl ester isocyanate, at 95°-96° C. (0.19 g, 30.9%) of 99% purity as judged by GC. IR (neat) 2241, 1744 cm-1. 1H NMR (CDCl3) δ 7.36 (s, 5H), 5.22 (s, 2H), 4.10 (q, 1H, J=14.3), 1.49 (d, 3H, J=7.1) ppm.

Aufarbeitung

  1. additionwas added to the reaction mixture
  2. customA white ppt formed
  3. filtrationwas filtered off
  4. concentrationThe filtrate was concentrated in vacuo
  5. extractionthe residue was extracted with 3×20 mL diethylether
  6. concentrationThe ether layers were concentrated
  7. distillationthe residue was distilled under vacuum (ca. 0.1-0.3 torr)
  8. customcollecting product, alanine benzyl ester isocyanate
  9. customat 95°-96° C.

Quellen und Nachweise

ORD-Eintrag
ord-eddfa9f282f2482b97292ecdb64a849f
Quelldatensatz
uspto-grants-1993_02
Patentnummer
US05189205

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