Sodium cyanoborohydride → HCID 135577948, Verbindung

HRID 1638603Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1638603
[C:1]([NH:4][C:5]1[NH:6][C:7](=[O:21])[C:8]([CH2:18][CH:19]=O)=[C:9]([N:11]([C:15](=[O:17])[CH3:16])[C:12](=[O:14])[CH3:13])[N:10]=1)(=[O:3])[CH3:2].[NH2:22][C:23]1[CH:42]=[CH:41][C:26]([C:27]([NH:29][C@H:30]([C:37]([O:39][CH3:40])=[O:38])[CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[O:28])=[CH:25][CH:24]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[C:1]([NH:4][C:5]1[NH:6][C:7](=[O:21])[C:8]([CH2:18][CH2:19][NH:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]([NH:29][C@H:30]([C:37]([O:39][CH3:40])=[O:38])[CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[O:28])=[CH:41][CH:42]=2)=[C:9]([N:11]([C:15](=[O:17])[CH3:16])[C:12](=[O:14])[CH3:13])[N:10]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 5003444Sodium cyanoborohydrideHCID 12469743dimethyl N-(4-aminobenzoyl)-L-glutamateHCID 135577947HCID 135577947, Verbindung

Produkt 1

HCID 135577948HCID 135577948, VerbindungAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 2-(2-acetylamino-4-diacetylamino-1,6-dihydro-6-oxo-5-pyrimidinyl)acetaldehyde (1.74 g, 5.92 mmol) and dimethyl N-(4-aminobenzoyl)-L-glutamate (J. Am. Chem. Soc., 1958, 80, 5779) (1.74 g, 5.92 mmol) in acetic acid (90 ml) was stirred for 10 minutes. Sodium cyanoborohydride (0.84 g, 13.4 mmol) was added in small portions over 1 hour. After an additional 30 minutes, the reaction was spin evaporated in vacuo to a thick oil. The oil was dissolved in ethyl acetate (500 ml) and washed with 5% aqueous sodium bicarbonate until neutral, water (50 ml), brine (50 ml), dried with magnesium sulfate and spin evaporated in vacuo. Recrystallization from ethyl acetate, with filtration to remove insolubles, yielded 1.5 g (49% of theory) of dimethyl N-[4-[2-(2-acetylamino-4-diacetylamino-1,6-dihydro-6-oxo-5-pyrimidinyl)ethylamino]benzoyl]-L-glutamate, mp 168°-178° C. Recrystallization from ethyl acetate (Norite) gave 0.830 g (25% of theory) of the analytical sample, mp 176°-179° C.

Aufarbeitung

  1. customevaporated in vacuo to a thick oil
  2. dissolutionThe oil was dissolved in ethyl acetate (500 ml)
  3. washwashed with 5% aqueous sodium bicarbonate until neutral, water (50 ml), brine (50 ml)
  4. dry with materialdried with magnesium sulfate
  5. customspin evaporated in vacuo
  6. customRecrystallization from ethyl acetate
  7. filtrationwith filtration
  8. customto remove insolubles

Quellen und Nachweise

ORD-Eintrag
ord-b881914833ec494da48277936ec7be46
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04880812

Notizen zur Reaktion

Wird geladen…