Hydrochloric Acid → Methyl (2s,3s,5s)-3-[(hydroxyamino)carbonyl]-5-methoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1-carboxylate

HRID 535083Notes

Reaction equation

HRID 535083 reaction equation
[CH3:1][O:2][C@@H:3]1[CH2:8][N:7]([C:9]([O:11][CH3:12])=[O:10])[C@H:6]([C:13]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[O:14])[C@@H:5]([C:27](OC)=[O:28])[CH2:4]1.[OH:31][NH2:32].Cl.NO.C[O-].[Na+].Cl>CO>[OH:31][NH:32][C:27]([C@H:5]1[CH2:4][C@H:3]([O:2][CH3:1])[CH2:8][N:7]([C:9]([O:11][CH3:12])=[O:10])[C@@H:6]1[C:13]([N:15]1[CH2:16][CH2:17][N:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:19][CH2:20]1)=[O:14])=[O:28]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 67304314Dimethyl (2s,3s,5s)-5-methoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

Product 1

HCID 87348843Methyl (2s,3s,5s)-3-[(hydroxyamino)carbonyl]-5-methoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1-carboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of dimethyl (2S,3S,5S)-5-methoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate (0.027 g, 0.000064 mol) in methanol (0.30 mL, 0.0074 mol) was added 1.640 M of N-hydroxyamine in methanol (0.7850 mL), freshly made from the corresponding hydroxylamine HCl salt and sodium methoxide. The mixture was stirred at rt for 1 h, then acidified with 1N HCl. The crude mixture was applied directly on RP-HPLC to afford the product as a TFA salt (23 mg, 68%). MS (ESI): (M+H)+=421.2.

Sources & evidence

ORD record
ord-28b45f6441ac4b17b49318036a19b1be
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Reaction notes

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