1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (1-{2-[(2-Isopropyl-5-methyl-cyclohexanecarbonyl)-amino]-1-phenyl-ethylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester

HRID 18494

Reaktionsgleichung

Reaktionsgleichung von HRID 18494
[C:1]([NH:8][C@@H:9]([C:11]([OH:13])=O)[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:35][CH:36]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[CH2:37][NH:38][C:39]([CH:41]1[CH2:46][CH:45]([CH3:47])[CH2:44][CH2:43][CH:42]1[CH:48]([CH3:50])[CH3:49])=[O:40]>O.C(OCC)(=O)C.C1COCC1>[C:4]([O:3][C:1](=[O:2])[NH:8][CH:9]([C:11](=[O:13])[NH:35][CH:36]([C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)[CH2:37][NH:38][C:39]([CH:41]1[CH2:46][CH:45]([CH3:47])[CH2:44][CH2:43][CH:42]1[CH:48]([CH3:50])[CH3:49])=[O:40])[CH3:10])([CH3:5])([CH3:6])[CH3:7]

Komponenten

8

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 637606BOC-D-alanineHCID 668315382-Isopropyl-5-methyl-cyclohexanecarboxylic acid (2-amino-2-phenyl-ethyl)-amide

Produkt 1

HCID 66831508(1-{2-[(2-Isopropyl-5-methyl-cyclohexanecarbonyl)-amino]-1-phenyl-ethylcarbamoyl}-ethyl)-carbamic acid tert-butyl esterAusbeute 25,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 15 mL reaction vessel equipped with a stir bar was charged with THF (15 mL), Boc-(R)-alanine (52 mg, 0.273 mmoles), HOBt (37.87 mg, 0.273 mmoles), EDCI (53 mg, 0.273 mmoles) and TEA (37 μl, 0.273 mmoles). The reaction mixture was stirred for 15 min. whereupon 2-isopropyl-5-methyl-cyclohexanecarboxylic acid (2-amino-2-phenyl-ethyl)-amide (75 mg, 0.248 mmol) was added and stirred for an additional 3 h. Ethyl acetate (10 mL) and H2O (10 mL) were added to the reaction mixture. The heterogeneous mixture was transferred to a separatory funnel where the aqueous phase was separated and re-extracted with ethyl acetate (2×10 mL). The organic phases were combined and washed with 1N HCl (2×10 mL), H2O (1×10 mL), sat NaHCO3 (3×10 mL), brine (10 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (20% ethyl acetate/hexane for elution) provided the title compounds as colorless solid (30 mg).

Aufarbeitung

  1. customA 15 mL reaction vessel
  2. customequipped with a stir bar
  3. additionwas added
  4. customThe heterogeneous mixture was transferred to a separatory funnel
  5. customwhere the aqueous phase was separated
  6. extractionre-extracted with ethyl acetate (2×10 mL)
  7. washwashed with 1N HCl (2×10 mL), H2O (1×10 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by flash chromatography on silica gel (20% ethyl acetate/hexane for elution)

Quellen und Nachweise

ORD-Eintrag
ord-1427a2edb9904b8ab1beb547cd8690e8
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741355B2

Verknüpfte Notizen

Wird geladen…