Hydrochloric Acid → 3-{4-[2-(Tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-isopropylsulfanyl-propionic acid ethyl ester

HRID 47821

Reaktionsgleichung

Reaktionsgleichung von HRID 47821
[CH2:1]([O:3][C:4](=[O:31])[CH:5](O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:9][CH:8]=1)[CH3:2].CS(Cl)(=O)=O.[CH3:37][CH:38]([SH:40])[CH3:39].CC(C)([O-])C.[K+].O1CCCC1.Cl>N1C=CC=CC=1.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:31])[CH:5]([S:40][CH:38]([CH3:39])[CH3:37])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:9][CH:8]=1)[CH3:2]

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 63642-PropanethiolHCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 698837723-{4-[2-(Tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-hydroxy-propionic acid ethyl ester

Produkt 1

HCID 698839343-{4-[2-(Tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-isopropylsulfanyl-propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-hydroxy-propionic acid ethyl ester (0.69 mmol, 300 mg) dissolved in pyridine (3 mL) was added methanesulfonyl chloride (0.69 mmol, 0.534 mL). The mixture was stirred at room temperature overnight. A portion of the reaction mixture (0.115 mmol) was added to a solution containing 2-propane thiol (0.115 mmol, 0.107 mL) dissolved in anhydrous CH2Cl2 (2 mL). To this stirred solution was added a 1M solution of potassium tert-butoxide in tetrahydrofuran (0.115 mmol, 0.115 mL). The mixture was stirred overnight then poured over 1 M HCl. The mixture was extracted with diethyl ether (3×). The organic layers were combined, washed with 1 M HCl (2×), saturated brine (2×), dried over Na2SO4, and concentrated to a crude film. The film was purified by chromatography on silica gel (Merck silica gel 60, art#9385-3) eluting with 20% ethyl acetate in hexanes to give 3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-isopropylsulfanyl-propionic acid ethyl ester as a clear film containing an approximate 1:1 mixture of methyl and ethyl ester (30.2 mg, 55%).

Aufarbeitung

  1. stirringThe mixture was stirred overnight
  2. extractionThe mixture was extracted with diethyl ether (3×)
  3. washwashed with 1 M HCl (2×), saturated brine (2×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to a crude film
  6. customThe film was purified by chromatography on silica gel (Merck silica gel 60, art#9385-3)
  7. washeluting with 20% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-60a6ae17810b4ae0a3d67bbb2ec30602
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699904B2

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