Benzyl Alcohol → (S)-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylmethyl)carbamic acid benzyl ester

HRID 412412

Reaktionsgleichung

Reaktionsgleichung von HRID 412412
[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]([CH2:7]C(O)=O)[C:4](=[O:11])[O:3]1.C([N:15]([CH2:18]C)CC)C.C1([O:26]P(N=[N+]=[N-])(=O)OC2C=CC=CC=2)C=CC=CC=1.[CH2:39]([OH:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C1(C)C=CC=CC=1>[CH2:39]([O:46][C:18](=[O:26])[NH:15][CH2:7][C@H:5]1[C:4](=[O:11])[O:3][C:2]([CH3:1])([CH3:12])[O:6]1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 641720(S)-2-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

Produkt 1

HCID 67483545(S)-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylmethyl)carbamic acid benzyl esterAusbeute 69,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To (S)-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)acetic acid (1 g, 5.7 mmol) and triethylamine (0.66 g, 6.5 mmol) in toluene (20 mL) was added phosphorazidic acid diphenyl ester (1.7 g, 6.2 mmol). The solution was heated to reflux for 1 hour. Benzyl alcohol (0.54 g, 5 mmol) was added and reflux was maintained for additional 6 hours. After cooling, the solution was partitioned between ethyl acetate (2×50 mL) and aqueous sodium hydrogen carbonate (10%, 2×50 mL). The organic layers were collected, dried (sodium sulphate) and the solvent removed by evaporation in vacuo to afford 976 mg of crude (S)-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylmethyl)carbamic acid benzyl ester as an oil.

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 hour
  3. temperaturereflux
  4. temperaturewas maintained for additional 6 hours
  5. temperatureAfter cooling
  6. customthe solution was partitioned between ethyl acetate (2×50 mL) and aqueous sodium hydrogen carbonate (10%, 2×50 mL)
  7. customThe organic layers were collected
  8. dry with materialdried (sodium sulphate)
  9. customthe solvent removed by evaporation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f28c776081874cc496ca29242572d1f3
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562807B2

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