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

HRID 276926

Reaktionsgleichung

Reaktionsgleichung von HRID 276926
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

Reaktionsbedingungen

Temperatur
2.5 °C

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. extractionThe reaction mixture was extracted with ethyl acetate (300 ml) and organic layer
  2. customwas separated
  3. washwhich was washed two times with saturated sodium chloride in water
  4. dry with materialdried over magnesium sulfate
  5. customSolvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d98944a48c444e3782edaf7c9c5a6e29
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355640B1

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