Chloroacetaldehyde → 2-[Benzyl-(2-chloro-ethyl)-amino]-propionic acid ethyl ester

HRID 408577

Reaktionsgleichung

Reaktionsgleichung von HRID 408577
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:6])[CH3:2].[O-]S([O-])(=O)=O.[Mg+2].[Cl:22][CH2:23][CH:24]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([N:7]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:24][CH2:23][Cl:22])[CH3:6])[CH3:2]

Komponenten

7

Edukt 5

HCID 33ChloroacetaldehydeHCID 176Acetic AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 222273Ethyl 2-(benzylamino)propanoateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 705577792-[Benzyl-(2-chloro-ethyl)-amino]-propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-benzylamino-propionic acid ethyl ester (1 eq.) in dry DCM was added MgSO4 (0.75 eq.). The reaction was cooled to 0° C. then the above solution of chloroacetaldehyde in dry DCM (solution I) and acetic acid (1 eq.) were added. Sodium triacetoxyborohydride (1.5 eq.) was added portionwise. The reaction was stirred for 1 h at 0° C. The crude was carefully quenched with a saturated aqueous solution of NaHCO3. Then aqueous NaOH (2N) was added. The aqueous layer was extracted with DCM. The combined organic layers were washed with an aqueous saturated solution of NaHCO3, then dried over MgSO4 and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc 98/2 to 95/5) to afford 2-[benzyl-(2-chloro-ethyl)-amino]-propionic acid ethyl ester.

Aufarbeitung

  1. customThe crude was carefully quenched with a saturated aqueous solution of NaHCO3
  2. additionThen aqueous NaOH (2N) was added
  3. extractionThe aqueous layer was extracted with DCM
  4. washThe combined organic layers were washed with an aqueous saturated solution of NaHCO3
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by chromatography on silica gel (elution with heptane/EtOAc 98/2 to 95/5)

Quellen und Nachweise

ORD-Eintrag
ord-ebec0e38facf4fb582b154836ae73339
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759334B2

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