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

HRID 535078Notes

Reaction equation

HRID 535078 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([C:13]([C@@H:15]3[C@@H:20]([C:21]([O:23]C)=O)[CH2:19][C@H:18]([S:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:17][N:16]3[C:32]([O:34][CH3:35])=[O:33])=[O:14])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.[OH:41][NH2:42].C[O-].[Na+].Cl>CO>[OH:41][NH:42][C:21]([C@H:20]1[CH2:19][C@H:18]([S:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:17][N:16]([C:32]([O:34][CH3:35])=[O:33])[C@@H:15]1[C:13]([N:10]1[CH2:9][CH2:8][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1)=[O:14])=[O:23]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 67304232HCID 67304232, compound

Product 1

HCID 86598258Methyl(2S,3S,5S)-3-[(hydroxyamino)carbonyl]-2-[(4-phenylpiperazin-1-yl)carbonyl]-5-(phenylthio)piperidine-1-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the reaction mixture of dimethyl (2S,3S,5S)-2-[(4-phenylpiperazin-1-yl)carbonyl]-5-(phenylthio)piperidine-1,3-dicarboxylate (51 mg, 0.00010 mol) in tetrahydrofuran (0.50 mL, 0.0062 mol) was added 1.640 M of N-hydroxyamine in methanol (1.25 mL) made from the corresponding salt and sodium methoxide. After stirred at rt for 1 h, the mixture was acidified with 1N HCl. The resultant mixture was applied directly on RP-HPLC to afford the product as a TFA salt (39 mg, 63%). MS (ESI): (M+H)+=499.1.

Sources & evidence

ORD record
ord-f3ac8e5ad8904e88a47554b7bd284119
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Reaction notes

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