Gamma-Aminobutyric Acid → 4-(((Benzyloxy)carbonyl)amino)butanoic acid

HRID 27348

Reaktionsgleichung

Reaktionsgleichung von HRID 27348
O.[NH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].C(=O)(O)[O-].[Na+].[CH2:14]([O:21][C:22](ON1C(=O)CCC1=O)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[C:22]([NH:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7])([O:21][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:23]

Komponenten

6

Edukt 4

HCID 119Gamma-Aminobutyric AcidHCID 962WaterHCID 83172Benzyl succinimido carbonateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 211844-(((Benzyloxy)carbonyl)amino)butanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 100 ml. of water and 120 ml. of tetrahydrofuran is added sequentially 12.4 g. of γ-aminobutyric acid, 10.4 g. of sodium bicarbonate, and 30 g. of N-benzyloxycarbonyloxysuccinimide. The reaction mixture is stirred for approximately 3.5 hours at room temperature and then the tetrahydrofuran is evaporated in vacuo. The residue is diluted with 200 ml. of water and extracted with (2×300 ml.) anhydrous ether. The aqueous layer is then acidified to pH 1-2 with 1 N hydrochloric acid and extracted with (3×400 ml.) methylene chloride. The methylene chloride extracts are collected and combined and then washed with (3×200 ml.) brine solution, dried with anhydrous magnesium sulfate and the solvent evaporated in vacuo at room temperature. The residue provides N-carbobenzoxy-γ-aminobutyric acid.

Aufarbeitung

  1. customthe tetrahydrofuran is evaporated in vacuo
  2. additionThe residue is diluted with 200 ml
  3. extractionof water and extracted with (2×300 ml.) anhydrous ether
  4. extractionextracted with (3×400 ml.) methylene chloride
  5. customThe methylene chloride extracts are collected
  6. washwashed with (3×200 ml.) brine solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customthe solvent evaporated in vacuo at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-ea43e1971c3f40c79b2c67c5c1bb1432
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04221706

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