Hydrochloric Acid → HCID 12837137, Verbindung

HRID 615345

Reaktionsgleichung

Reaktionsgleichung von HRID 615345
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[NH:12][C@H:11]([C:13]([OH:15])=[O:14])[CH2:10][S:9]1.[OH-:16].[Na+].[C:18](Cl)(=[O:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](Cl)=[O:26].Cl>C(=O)([O-])[O-].[K+].[K+]>[C:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([N:12]1[C@H:11]([C:13]([OH:15])=[O:14])[CH2:10][S:9][CH:8]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[OH:1])=[O:26])([OH:28])=[O:16]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 534653Octanedioyl dichlorideHCID 2825745(4R)-2-(2-hydroxyphenyl)-1,3-thiazolidine-4-carboxylic acid

Produkt 1

HCID 12837137HCID 12837137, VerbindungAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11430Potassium CarbonateLösungsmittel

Versuchsvorschrift

(4R)-2-(2-Hydroxyphenyl)-4-thiazolidinecarboxylic acid (6.8 g), in N sodium hydroxide (30 ml) and octanedioyl dichloride (6.3 g), were added dropwise to 1M potassium carbonate (60 ml) with stirring under ice-cooling. After the addition, the reaction mixture was stirred for 1 hour at the same temperature and for additional 1 hour at room temperature. The solution was acidified with dilute hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residual oil*2 was purified by silica gel column chromatography to give 7.0 g (61%) of the titled compound: mp 155°-157° C. (dec.) (ethyl acetate); [α]D27 +134.1° (c=0.5, methanol). IR (nujol, cm-1): 3220 (OH), 1710 (COOH), 1620 (CON), 1600 (aromatic), 1415, 1235, 1172, 950, 760. NMR (DMSO-d6,δ): 0.53-1.73 (8H, m, -- CH2 --CH2)4CH2 --), 1.77-2.57 (4H, m, --CH2 --CH2)4CH2 --), 3.03 (1H, ABq (A part), d, J=11.5, 8.5 Hz, C5*1 --HA), 3.37 (1H, ABq (B part), d, J=11.5, 6.5 Hz, C5 --HB), 4.60 (1H, dd, J=8.5, 6.5 Hz, C4 --H), 6.28 (1H, s, C2 --H), 6.45-8.07 (4H, m, arom. H), 9.77 (1H, s, C2 --H), 6.45-8.07 (4H, m, arom. H), 9.77 (1H, s, --COOH). TLC: Rf value*3 0.52. pyrrolidine ring. The same shall be applied hereinafter.

Aufarbeitung

  1. temperaturecooling
  2. additionAfter the addition
  3. stirringthe reaction mixture was stirred for 1 hour at the same temperature and for additional 1 hour at room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residual oil*2 was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1d3bde403eac4e73977fbb81c22d7767
Quelldatensatz
uspto-grants-1985_02
Patentnummer
US04499102

Verknüpfte Notizen

Wird geladen…