Benzyl chloroformate → Ethyl 3-{[(benzyloxy)carbonyl]amino}propanoate

HRID 965335

Reaktionsgleichung

Reaktionsgleichung von HRID 965335
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[OH-].[Na+].[CH2:12]([O:19][C:20](Cl)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCCC1.O>[CH2:12]([O:19][C:20]([NH:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 458475beta-Alanine, ethyl ester, hydrochloride

Produkt 1

HCID 12116647Ethyl 3-{[(benzyloxy)carbonyl]amino}propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ethyl 3-aminopropionate hydrochloride (10 g) was dissolved in a mixture of tetrahydrofuran (100 ml) and water, which was cooled at 0° to 5° C. in an ice bath and adjusted to pH 8.2 with 30% aqueous sodium hydroxide solution. To a resulting solution was added with care benzyloxycarbonyl chloride (10.3 ml), with maintaining the pH from pH 8.0 to 9.0 with 30% aqueous sodium hydroxide solution at 0° to 5° C. The reaction mixture was extracted with ethyl acetate (300 ml) and organic layer was separated, which was washed two times with saturated sodium chloride in water and dried over magnesium sulfate. Solvent was removed under reduced pressure to give ethyl 3-(benzyloxycarbonylamino)-propionate (15.3 g).

Aufarbeitung

  1. temperaturewas cooled at 0° to 5° C. in an ice bath
  2. extractionThe reaction mixture was extracted with ethyl acetate (300 ml) and organic layer
  3. customwas separated
  4. washwhich was washed two times with saturated sodium chloride in water
  5. dry with materialdried over magnesium sulfate
  6. customSolvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b5f446095697466692242d5efe51023c
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05773530

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