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

HRID 1726703Notes

Reaction equation

HRID 1726703 reaction equation
[OH:1][NH2:2].[C:3]1([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C@H:17]3[CH2:22][CH2:21][C@@H:20]([O:23][CH2:24][C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)[CH2:19][C@@H:18]3[C:31](OC)=[O:32])=[O:16])[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CO>>[OH:1][NH:2][C:31]([C@H:18]1[CH2:19][C@H:20]([O:23][CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH2:21][CH2:22][C@@H:17]1[C:15]([N:12]1[CH2:13][CH2:14][N:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:10][CH2:11]1)=[O:16])=[O:32]

Participants

4

Reactant 3

HCID 787HydroxylamineHCID 887MethanolHCID 67305585methyl(1S,2S,5R)-2-[(4-phenylpiperazin-1-yl)carbonyl]-5-(pyridin-3-ylmethoxy)cyclohexanecarboxylate

Product 1

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

Procedure

1.5 M of hydroxyamine solution (0.7 ml) was added 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. LCMS: (M+H)+=439.3.

Workup

  1. customthen purified by Prep-HPLC

Sources & evidence

ORD record
ord-d4497f94ad3a41f9b56a143484639c76
Source dataset
uspto-grants-2009_02
Patent number
US07491724B2

Reaction notes

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