Hydrochloric Acid → 1-[[(1-Carboxy-3-phenylpropyl)amino]acetyl]-5-(2-hydroxyphenyl)-2-pyrrolidinecarboxylic acid

HRID 615354

Reaktionsgleichung

Reaktionsgleichung von HRID 615354
Cl[CH2:2][C:3]([N:5]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[CH2:8][CH2:7][CH:6]1[C:17]([OH:19])=[O:18])=[O:4].[NH2:20][CH:21]([CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:22]([OH:24])=[O:23].Cl>[OH-].[Na+]>[C:22]([CH:21]([NH:20][CH2:2][C:3]([N:5]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[CH2:8][CH2:7][CH:6]1[C:17]([OH:19])=[O:18])=[O:4])[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([OH:24])=[O:23]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 102530Homophenylalanine, DL-HCID 204280761-(Chloroacetyl)-5-(2-hydroxyphenyl)-2-pyrrolidinecarboxylic acid

Produkt 1

HCID 204280901-[[(1-Carboxy-3-phenylpropyl)amino]acetyl]-5-(2-hydroxyphenyl)-2-pyrrolidinecarboxylic acidAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

1-(Chloroacetyl)-5-(2-hydroxyphenyl)-2-pyrrolidinecarboxylic acid [mp 204°-206° C.(dec.), [α]D24 +24.5° (c=1.2, MeOH)] (2.8 g) was added to a stirred solution of 2-amino-4-phenylbutanoic acid (1.8 g) in N sodium hydroxide (40 ml). The reaction mixture was stirred overnight at room temperature. The solution was adjusted to pH 1.5 by 20% hydrochloric acid, and washed with ethyl acetate. The aqueous layer was adjusted to pH 3.0, and the separated solid was collected by filtration to give 1.0 g (24%) of the titled compound. IR (nujol, cm-1): 3425, 1735, 1625, 1588.

Aufarbeitung

  1. washwashed with ethyl acetate
  2. filtrationthe separated solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-414ae1f82d3545c5b10e9ca01c6191e0
Quelldatensatz
uspto-grants-1985_02
Patentnummer
US04499102

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