Hydroxylamine → (1S,2S,5R)-N-hydroxy-2-[(4-phenylpiperazin-1-yl)carbonyl]-5-(pyridin-3-ylmethoxy)cyclohexanecarboxamide

HRID 61501

Reaktionsgleichung

Reaktionsgleichung von HRID 61501
CC(C)([O-])C.[K+].O[C@H]1C[C@H](C(OC)=O)[C@@H](C(N2CCN(C3C=CC=CC=3)CC2)=O)CC1.Cl.ClCC1C=NC=CC=1.[OH:41][NH2:42].[C:43]1([N:49]2[CH2:54][CH2:53][N:52]([C:55]([C@H:57]3[CH2:62][CH2:61][C@@H:60]([O:63][CH2:64][C:65]4[CH:66]=[N:67][CH:68]=[CH:69][CH:70]=4)[CH2:59][C@@H:58]3[C:71](OC)=[O:72])=[O:56])[CH2:51][CH2:50]2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.CO>O1CCCC1>[OH:41][NH:42][C:71]([C@H:58]1[CH2:59][C@H:60]([O:63][CH2:64][C:65]2[CH:66]=[N:67][CH:68]=[CH:69][CH:70]=2)[CH2:61][CH2:62][C@@H:57]1[C:55]([N:52]1[CH2:53][CH2:54][N:49]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH2:50][CH2:51]1)=[O:56])=[O:72]

Komponenten

8

Edukt 6

HCID 787HydroxylamineHCID 887MethanolHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 23665647Potassium tert-butoxideHCID 67304253methyl(1S,2S,5R)-5-hydroxy-2-[(4-phenylpiperazin-1-yl)carbonyl]cyclohexanecarboxylateHCID 67305585methyl(1S,2S,5R)-2-[(4-phenylpiperazin-1-yl)carbonyl]-5-(pyridin-3-ylmethoxy)cyclohexanecarboxylate

Produkt 1

HCID 86598268(1S,2S,5R)-N-hydroxy-2-[(4-phenylpiperazin-1-yl)carbonyl]-5-(pyridin-3-ylmethoxy)cyclohexanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

1.00 M of Potassium tert-butoxide in tetrahydrofuran (0.212 mL) was added to a mixture of methyl(1S,2S,5R)-5-hydroxy-2-[(4-phenylpiperazin-1-yl)carbonyl]cyclohexanecarboxylate (36.8 mg, 0.000106 mol) and 3-chloromethylpyridine hydrochloride (17.4 mg, 0.106 mmol) in tetrahydrofuran (1.0 mL, 0.012 mol) at 0 Celsius. The mixture was stirred at room temperature for 1 hr then purified by HPLC. 1.5 M of hydroxyamine solution (0.7 ml) was added into to a solution of methyl(1S,2S,5R)-2-[(4-phenylpiperazin-1-yl)carbonyl]-5-(pyridin-3-ylmethoxy)cyclohexanecarboxylate (0.075 mmol, 0.000075 mol) made above in methanol (0.5 mL, 0.01 mol). It was stirred at rt for 2 hrs then purified by Prep-HPLC.

Aufarbeitung

  1. customthen purified by HPLC
  2. stirringIt was stirred at rt for 2 hrs
  3. customthen purified by Prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-7d23e9155f67488ea69ffa1c4a4e0b7d
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440958B2

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