Dicyclohexylcarbodiimide → (2R)-4-(4-oxo-4-(tetrahydro-2H-pyran-2-yloxyamino)butyl)phenyl 3-(5-(benzyloxy)pyridin-2-yl)-2-(tert-butoxycarbonylamino)propanoate

HRID 885711Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 885711
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C@@H:16]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:17]([OH:19])=[O:18])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][CH2:37][C:38]([NH:40][O:41][CH:42]2[CH2:47][CH2:46][CH2:45][CH2:44][O:43]2)=[O:39])=[CH:31][CH:30]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:17]([O:19][C:29]2[CH:30]=[CH:31][C:32]([CH2:35][CH2:36][CH2:37][C:38](=[O:39])[NH:40][O:41][C@@H:42]3[CH2:47][CH2:46][CH2:45][CH2:44][O:43]3)=[CH:33][CH:34]=2)=[O:18])=[N:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 67001556(R)-3-(5-(Benzyloxy)pyridin-2-yl)-2-(tert-butoxycarbonylamino)propanoic acidHCID 866595084-(4-hydroxyphenyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Produkt 1

HCID 86659509(2R)-4-(4-oxo-4-(tetrahydro-2H-pyran-2-yloxyamino)butyl)phenyl 3-(5-(benzyloxy)pyridin-2-yl)-2-(tert-butoxycarbonylamino)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(R)-3-(5-(Benzyloxy)pyridin-2-yl)-2-(tert-butoxycarbonylamino)propanoic acid (0.19 g, 0.5 mmol), 4-(4-hydroxyphenyl)-N-(tetrahydro-2H-pyran-2-yloxy)-butanamide (0.14 g, 0.5 mmol), and DMAP (0.06 g, 0.5 mmol) were added into DCM (10 mL) and stirred at 0° C. for 10 min. A solution of DCC (0.12 g, 0.6 mmol) in DCM (5 mL) was added to the above-mentioned solution dropwise. The mixture was stirred from 0° C. at room temperature for 1 h (monitored by TLC). The white solid was removed and the filtrated was then evaporated in vacuo. Ethyl acetoacetate was added and the solid was again removed. The solution was evaporated in vacuo. The residue was purified by chromatography (EA:Hex=1:5) to give the title compound.

Aufarbeitung

  1. stirringThe mixture was stirred from 0° C. at room temperature for 1 h (monitored by TLC)
  2. customThe white solid was removed
  3. customthe filtrated was then evaporated in vacuo
  4. additionEthyl acetoacetate was added
  5. customthe solid was again removed
  6. customThe solution was evaporated in vacuo
  7. customThe residue was purified by chromatography (EA:Hex=1:5)

Quellen und Nachweise

ORD-Eintrag
ord-7f74e26e32644d36818201dd646a826b
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242282B2

Notizen zur Reaktion

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