Glycine, N-acetyl-N-phenyl- → (1R, 2R, 3S)-2,3-bis(hydroxymethyl)-1-cyclobutylamine N-acetyl-L-phenylglycine

HRID 374265

Reaktionsgleichung

Reaktionsgleichung von HRID 374265
[OH:1][CH2:2][CH:3]1[CH:6]([CH2:7][OH:8])[CH2:5][CH:4]1[NH2:9].[CH3:10][C:11]([N:13]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:14][C:15]([OH:17])=[O:16])=[O:12]>CO>[OH:1][CH2:2][C@@H:3]1[C@@H:6]([CH2:7][OH:8])[CH2:5][C@H:4]1[NH2:9].[CH3:10][C:11]([N:13]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:14][C:15]([OH:17])=[O:16])=[O:12]

Komponenten

4

Edukt 2

HCID 68483Glycine, N-acetyl-N-phenyl-HCID 197942472,3-Bis(hydroxymethyl)-1-cyclobutylamine

Produkt 1

HCID 131717654(1R, 2R, 3S)-2,3-bis(hydroxymethyl)-1-cyclobutylamine N-acetyl-L-phenylglycine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

913 mg of (1RS, 2RS, 3SR)-2,3-bis(hydroxymethyl)-1-cyclobutylamine was dissolved in 30 ml of methanol. Then 1340 mg of N-acetyl-L-phenylglycine was added thereto to form salt. The reaction mixture was concentrated under reduced pressure. 15 ml of isopropyl alcohol was added to the residue followed by fractional recrystallization. Thus 403.8 mg of (1R, 2R, 3S)-2,3-bis(hydroxymethyl)-1-cyclobutylamine/N-acetyl-L-phenylglycine salt was obtained.

Aufarbeitung

  1. customto form salt
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. addition15 ml of isopropyl alcohol was added to the residue
  4. customfollowed by fractional recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-f8c228103fd845eda2655b4240e94594
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166397

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