Hydrochloric Acid → (S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acid

HRID 714129

Reaktionsgleichung

Reaktionsgleichung von HRID 714129
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH2:12])[C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+].Cl[C:19]([O:21][CH3:22])=[O:20].Cl>C1COCC1>[CH3:22][O:21][C:19]([NH:12][C@H:8]([C:9]([OH:11])=[O:10])[CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)=[O:20]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6140L-PhenylalanineHCID 6586Methyl chloroformateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 10017620(S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acidAusbeute 198,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A suspension of L-diphenylalanine (13.87 g, 57.5 mmol) in THF (100 ml), and saturated NaHCO3 (3 mL) stirred at 0° C. was treated with neat methyl chloroformate (11.81 g, 125 mmol) (slow addition), stirred at the same temperature for 10 min and then at room temperature for 14 h, made acidic by addition of 1M HCl and extracted with DCM, dried over MgSO4 filtered and concentrated to give title compound (17.1 g, 99% yield) as white solid. Used without further purification. MS: m/z=322.1 (MNa+).

Aufarbeitung

  1. stirringstirred at the same temperature for 10 min
  2. extractionextracted with DCM
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1920437b70054c55954a76cd97adb72e
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187415B2

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