Hydrogen Sulfide → methyl [[1-[N-[p-(thiocarbamoyl)benzoyl]-glycyl]-4-piperidinyl]oxy]acetate

HRID 1768724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1768724
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([C:7]([NH:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH:16]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH2:15][CH2:14]2)=[O:12])=[O:8])=[CH:5][CH:4]=1)#[N:2].[SH2:27]>N1C=CC=CC=1.C(N(CC)CC)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][CH2:10][C:11]([N:13]2[CH2:14][CH2:15][CH:16]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH2:17][CH2:18]2)=[O:12])=[O:8])=[CH:25][CH:26]=1)(=[S:27])[NH2:2]

Komponenten

4

Edukt 2

HCID 402Hydrogen SulfideHCID 57145608methyl [[1-[N-(p-cyanbenzoyl)glycyl]-4-piperidinyl]oxy]acetate

Produkt 1

HCID 53924674methyl [[1-[N-[p-(thiocarbamoyl)benzoyl]-glycyl]-4-piperidinyl]oxy]acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22561186Pyridine triethylamineLösungsmittel

Versuchsvorschrift

A solution of 1.5 g of methyl [[1-[N-(p-cyanbenzoyl)glycyl]-4-piperidinyl]oxy]acetate in 215 ml of pyridine/triethylamine 40:3 is saturated with hydrogen sulphide and left at room temperature for 24 hours. After removing the solvent, the residue is taken up in ethyl acetate and washed with saturated sodium chloride solution. The organic extracts are dried and concentrated. After chromatography of the residue on silica gel with ethyl acetate followed by ethyl acetate/methanol, there are isolated 1.34 g of methyl [[1-[N-[p-(thiocarbamoyl)benzoyl]-glycyl]-4-piperidinyl]oxy]acetate, MS (FAB): 394 (M+H)+.

Aufarbeitung

  1. customAfter removing the solvent
  2. washwashed with saturated sodium chloride solution
  3. customThe organic extracts are dried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c5981bc11df044c2b1a8b5d5d5c913de
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05378712

Notizen zur Reaktion

Wird geladen…