Hydrochloric Acid → Phenylacetyl-glycine-t-butyl ester

HRID 248818

Reaktionsgleichung

Reaktionsgleichung von HRID 248818
[C:1]([O:5][C:6](=[O:17])[CH2:7][NH:8]C(=O)C1C=CC=CC=1)([CH3:4])([CH3:3])[CH3:2].[C:18]1([CH2:24][C:25]([OH:27])=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CN1CCOCC1.ClC(OCC(C)C)=O.C(OC(=O)CN)(C)(C)C.Cl>C(OCC)(=O)C.C(Cl)Cl>[C:1]([O:5][C:6](=[O:17])[CH2:7][NH:8][C:25](=[O:27])[CH2:24][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 999Phenylacetic AcidHCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 151417Glycine tert-butyl esterHCID 11020853Benzoyl-glycine-t-butyl ester

Produkt 1

HCID 19762247Phenylacetyl-glycine-t-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Following the procedure described for benzoyl-glycine-t-butyl ester, a solution of phenylacetic acid (11.44 grams) in ethyl acetate (approx. 100 ml) was activated by the mixed anhydride method using N-methylmorpholine (11.66 ml) followed by isobutyl chloroformate (10.89 ml) at -20° C. and coupled with glycine t-butyl ester.HCl (14.04 g) in methylene chloride (approx. 150 ml) which had been neutralized by addition of N-methylmorpholine (11.66 ml). After work-up, the product was obtained as an oil which was used for the next step without further purification.

Aufarbeitung

  1. customAfter work-up, the product was obtained as an oil which
  2. customwas used for the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-788a972defb74bada23a51c3657af5e9
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05212158

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