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Hydrochloric Acid → (2S)-(E)-[4-(2-carboxyethen-1-yl)thiazol-2-ylthio]-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}acetamide

HRID 545118
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 545118
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:5][N:6]1[CH2:11][CH2:10][O:9][C@@H:8]([CH2:12][NH:13][C:14](=[O:24])[CH2:15][S:16][C:17]2[S:18][CH:19]=[C:20]([CH:22]=O)[N:21]=2)[CH2:7]1.C(O)(=O)[CH2:30][C:31]([OH:33])=[O:32].N1CCCCC1.Cl>N1C=CC=CC=1.O>[C:31](/[CH:30]=[CH:22]/[C:20]1[N:21]=[C:17]([S:16][CH2:15][C:14]([NH:13][CH2:12][C@@H:8]2[O:9][CH2:10][CH2:11][N:6]([CH2:5][C:4]3[CH:25]=[CH:26][C:27]([Cl:28])=[C:2]([Cl:1])[CH:3]=3)[CH2:7]2)=[O:24])[S:18][CH:19]=1)([OH:33])=[O:32]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 86616376(2S)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}-(4-formylthiazol-2-ylthio)acetamide

Produkt 1

HCID 59009139(2S)-(E)-[4-(2-carboxyethen-1-yl)thiazol-2-ylthio]-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}acetamide

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

The resultant product (643 mg) of (70-2) was dissolved in pyridine (5 mL), malonic acid (291 mg) and piperidine (14 μL) were added, and the mixture was stirred at 100° C. for 3.5 hrs. The reaction mixture was poured into water, 1M hydrochloric acid was added to adjust to pH=4, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solvent of chloroform and methanol as an eluent. The solvent was evaporated from the eluent to give the title compound (618 mg) as a white amorphous solid.

Aufarbeitung

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography
  7. customThe solvent was evaporated from the eluent

Quellen und Nachweise

ORD-Eintrag
ord-ca47636c2f274beab94dde1a03579a3b
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07935700B2

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