Hydrochloric Acid → (3s,5s,6s)-5-[(Hydroxyamino)carbonyl]-1-methyl-6-[(4-phenyl-3,6-dihydropyridin-1(2h)-yl)carbonyl]piperidin-3-yl piperidine-1-carboxylate

HRID 61457Notes

Reaction equation

HRID 61457 reaction equation
C[O:2][C:3]([C@@H:5]1[C@@H:10]([C:11]([N:13]2[CH2:18][CH:17]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[N:9]([CH3:25])[CH2:8][C@@H](C2CCCCN2C([O-])=O)[CH2:6]1)=O.[OH:35][NH2:36].[CH3:37][O-:38].[Na+].Cl.[CH3:41][OH:42]>>[N:13]1([C:37]([O:42][C@H:41]2[CH2:6][C@H:5]([C:3]([NH:36][OH:35])=[O:2])[C@@H:10]([C:11]([N:13]3[CH2:14][CH:15]=[C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:17][CH2:18]3)=[O:12])[N:9]([CH3:8])[CH2:25]2)=[O:38])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 887Methanol2×HCID 10942334Sodium MethoxideHCID 131737177HCID 131737177, compound

Product 1

HCID 87348795(3s,5s,6s)-5-[(Hydroxyamino)carbonyl]-1-methyl-6-[(4-phenyl-3,6-dihydropyridin-1(2h)-yl)carbonyl]piperidin-3-yl piperidine-1-carboxylateYield 48%

Procedure

To a solution of (3S,5S,6S)-5-(methoxycarbonyl)-1-methyl-6-[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)carbonyl]piperidin-3-ylpiperidine-1-carboxylate (94 mg, 0.00020 mol) in methanol (0.8109 mL, 0.02002 mol) was added 1.640 M of N-hydroxyamine in methanol (2.44 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 (56 mg, 48%). MS (ESI): (M+H)+=471.1.

Sources & evidence

ORD record
ord-180348f3db6d4a41aadd206df6138286
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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