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

HRID 535075Notes

Reaction equation

HRID 535075 reaction equation
[O:1]=[C:2]([N:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)[CH2:3][O:4][C@@H:5]1[CH2:10][N:9]([C:11]([O:13][CH3:14])=[O:12])[C@H:8]([C:15]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[O:16])[C@@H:7]([C:29](OC)=[O:30])[CH2:6]1.[OH:38][NH2:39].C[O-].[Na+].Cl>CO>[OH:38][NH:39][C:29]([C@H:7]1[CH2:6][C@H:5]([O:4][CH2:3][C:2](=[O:1])[N:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[CH2:10][N:9]([C:11]([O:13][CH3:14])=[O:12])[C@@H:8]1[C:15]([N:17]1[CH2:18][CH2:19][N:20]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:21][CH2:22]1)=[O:16])=[O:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 10942334Sodium MethoxideHCID 67304375dimethyl(2S,3S,5S)-5-(2-oxo-2-pyrrolidin-1-ylethoxy)-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

Product 1

HCID 86598255Methyl(2S,3S,5S)-3-[(hydroxyamino)carbonyl]-5-(2-oxo-2-pyrrolidin-1-ylethoxy)-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1-carboxylateYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To the reaction mixture of dimethyl (2S,3S,5S)-5-(2-oxo-2-pyrrolidin-1-ylethoxy)-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate (64 mg, 0.00012 mol) in methanol (0.5018 mL, 0.01239 mol) was added 1.640 M of N-hydroxyamine in methanol solution (1.51 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 (14 mg, 18%). MS (ESI): (M+H)+=518.2.

Sources & evidence

ORD record
ord-fd2492b4596543058dad30e030fb51a1
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Reaction notes

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