1,2-Dichloroethane → cyclopentyl (2S)-[(tert-butoxycarbonyl)amino](cyclohexyl)acetate

HRID 475046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475046
[C:1]([O:5][C:6]([NH:8][C@@H:9](CC1CCCCC1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:20]1([OH:25])[CH2:24][CH2:23][CH2:22][CH2:21]1.[CH2:26](Cl)[CH2:27]Cl>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:27]1[CH2:26][CH2:22][CH2:21][CH2:20][CH2:24]1)[C:10]([O:25][CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 7298CyclopentanolHCID 10588189(2S)-2-(((tert-butoxy)carbonyl)amino)-3-cyclohexylpropanoic acid

Produkt 1

HCID 57658394cyclopentyl (2S)-[(tert-butoxycarbonyl)amino](cyclohexyl)acetateAusbeute 235,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (S)-2-tert-butoxycarbonylamino-3-cyclohexyl-propionic acid (5 g, 19.4 mmol) in DMF (50 mL) at 0° C. was added cyclopentanol (8.8 ml, 97.15 mmol), EDC (4.09 g, 21.37 mmol) and finally DMAP (237 mg, 1.94 mmol). The reaction mixture was warmed to RT and stirred for 18 h. The DMF was removed in vacuo to give a clear oil. This was separated between water and EtOAc. The organic phase was dried (MgSO4) and concentrated in vacuo. The crude extract was purified by column chromatography (25% EtOAC in heptane) to yield the desired product as a clear oil (14.87 g, 55%). 1H NMR (300 MHz, d6-DMSO) δ: 7.09 (1H, d), 5.08 (1H, t), 3.76 (1H, t), 1.50-1.85 (10H, br m), 1.39 (9H, s), 1.00-1.25 (9H, br m).

Aufarbeitung

  1. customThe DMF was removed in vacuo
  2. customto give a clear oil
  3. customThis was separated between water and EtOAc
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. extractionThe crude extract
  7. customwas purified by column chromatography (25% EtOAC in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-516d9d60025d492aa40512b535ee8875
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637547B2

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