Hydrochloric Acid → (3S)-8-(3-methylbutylidene)-4-(4-methylpentanoyl)-1-thia-4-azaspiro[4.5]-decane-3-carboxylic acid

HRID 2249613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2249613
[CH3:1][CH:2]([CH3:18])[CH2:3][CH:4]=[C:5]1[CH2:17][CH2:16][C:8]2([S:12][CH2:11][C@H:10]([C:13]([OH:15])=[O:14])[NH:9]2)[CH2:7][CH2:6]1.C(N(CC)CC)C.[C:26](Cl)(=[O:32])[CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30].Cl>C(Cl)Cl>[CH3:1][CH:2]([CH3:18])[CH2:3][CH:4]=[C:5]1[CH2:17][CH2:16][C:8]2([S:12][CH2:11][C@H:10]([C:13]([OH:15])=[O:14])[N:9]2[C:26](=[O:32])[CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:7][CH2:6]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 170008Pentanoyl chloride, 4-methyl-HCID 68987170(3S)-8-(3-methylbutylidene)-1-thia-4-azaspiro[4.5]decane-3-carboxylic Acid

Produkt 1

HCID 57684379(3S)-8-(3-methylbutylidene)-4-(4-methylpentanoyl)-1-thia-4-azaspiro[4.5]-decane-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

In 8 ml of methylene chloride are dissolved 0.79 g of (3S)-8-(3-methylbutylidene)-1-thia-4-azaspiro[4.5]decane-3-carboxylic acid and 1.20 ml of triethylamine. Into the solution thus obtained are dropwise added a solution of isocaproyl chloride (prepared from 0.48 ml of isocaproic acid, 0.38 ml of oxalyl chloride and 5 ml of methylene chloride) in methylene chloride at 5-10° C., and stirred at ambient temperature for 2 hours. The whole was acidified to pH 2.0 with 2 mol/L HCl and extracted with CHCl3. The combined organic extracts were washed with water and brine, dried on MgSO4 and concentrated under reduced pressure. The residue was purified by chromatography, [eluent; chloroform:methanol=9:1] to obtain 1.10 g of (3S)-8-(3-methylbutylidene)-4-(4-methylpentanoyl)-1-thia-4-azaspiro[4.5]-decane-3-carboxylic acid as a colorless crystalline product.

Aufarbeitung

  1. customInto the solution thus obtained
  2. extractionextracted with CHCl3
  3. washThe combined organic extracts were washed with water and brine
  4. customdried on MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography, [eluent; chloroform:methanol=9:1]

Quellen und Nachweise

ORD-Eintrag
ord-fadef12ee2844f648509d30acee432d9
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07314888B1

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