Hydroxylamine → HCID 87349003, compound

HRID 61497Notes

Reaction equation

HRID 61497 reaction equation
[OH:1][NH2:2].[O:3]([C@H:10]1[CH2:15][C@H:14]([C:16](OC)=[O:17])[C@@H:13]([C:20]([N:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:24][CH2:23]2)=[O:21])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(O)(C(F)(F)F)=O>CO>[OH:1][NH:2][C:16]([C@H:14]1[CH2:15][C@H:10]([O:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:11][CH2:12][C@@H:13]1[C:20]([N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:24][CH2:23]1)=[O:21])=[O:17]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 6422Trifluoroacetic acidHCID 67304032Methyl (1s,2s,5r)-5-phenoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]cyclohexane-carboxylate

Product 1

HCID 87349003HCID 87349003, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of hydroxyamine in MeOH (1.5 M, 0.75 ml) was added to methyl(1S,2S,5R)-5-phenoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]cyclohexane-carboxylate (0.29 mmol, 0.00029 mol) in MeOH (0.5 mL) at RT. The resulting mixture was stirred at RT for 2 hrs, and was adjusted to PH=2.0 with TFA, and then was purified by Prep-HPLC to give the desired product. LCMS: (M+H)+=424.2.

Workup

  1. customwas purified by Prep-HPLC

Sources & evidence

ORD record
ord-9bba759908524ebd9f4ef524444271d2
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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