Hydrochloric Acid → 4-({[4-(But-2-ynyloxy)phenyl]thio}methyl)-N-hydroxypiperidine-4-carboxamide

HRID 353554Notes

Reaction equation

HRID 353554 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([CH2:18][S:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]#[C:29][CH3:30])=[CH:22][CH:21]=2)([C:14]([NH:16][OH:17])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(Cl)Cl.CO.O1CCOCC1>[CH2:27]([O:26][C:23]1[CH:24]=[CH:25][C:20]([S:19][CH2:18][C:11]2([C:14]([NH:16][OH:17])=[O:15])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:21][CH:22]=1)[C:28]#[C:29][CH3:30]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 23513813Tert-butyl-4-({[4-(2-butynyloxy)phenyl]sulfanyl)methyl)-4-[(hydroxyamino)carbonyl]-1-piperidinecarboxylate

Product 1

HCID 235139124-({[4-(But-2-ynyloxy)phenyl]thio}methyl)-N-hydroxypiperidine-4-carboxamideYield 842.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.143 g (0.033 mmol) of tert-butyl-4-({[4-(2-butynyloxy) phenyl]sulfanyl}methyl)-4-[(hydroxyamino)-carbonyl]-1-piperidinecarboxylate in 5 mL of CH2Cl2 and 1 ml of MeOH was added 5 mL of 4M HCl in dioxane and stirred for 1 h. The reaction was concentrated in vacuo and the residue was triturated with ether and filtered to provide 0.093 g (76%) of the desired product as a pale orange solid. Electrospray Mass Spec: 335.3 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue was triturated with ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-f13ffc6bacba41519872f1d1623ccdae
Source dataset
uspto-grants-2004_06
Patent number
US06753337B2

Reaction notes

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