N-tert-butoxy-1-[4-(4-chlorobenzoyl)piperidine-1-sulfonyl]piperidine-2-(R)-carboxamide → N-hydroxy-1-[4-(4-chlorobenzoyl)-piperidine-1-sulfonyl]piperidine-2-(R)-carboxamide

HRID 366480

Reaction equation

HRID 366480 reaction equation
C([O:5][NH:6][C:7]([C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]1[S:15]([N:18]1[CH2:23][CH2:22][CH:21]([C:24](=[O:32])[C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[CH2:20][CH2:19]1)(=[O:17])=[O:16])=[O:8])(C)(C)C>ClCCCl>[OH:5][NH:6][C:7]([C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]1[S:15]([N:18]1[CH2:19][CH2:20][CH:21]([C:24](=[O:32])[C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)[CH2:22][CH2:23]1)(=[O:17])=[O:16])=[O:8]

Participants

3

Reactant 1

HCID 18727273N-tert-butoxy-1-[4-(4-chlorobenzoyl)piperidine-1-sulfonyl]piperidine-2-(R)-carboxamide

Product 1

HCID 15434917N-hydroxy-1-[4-(4-chlorobenzoyl)-piperidine-1-sulfonyl]piperidine-2-(R)-carboxamideYield 51%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of N-tert-butoxy-1-[4-(4-chlorobenzoyl)piperidine-1-sulfonyl]piperidine-2-(R)-carboxamide (100 mg, 0.22 mmol), [prepared as described in Step 1 above], in 1,2-dichloroethane (10 ml) was cooled to -30° C. and HCl gas was bubbled through it for 10 min. The reaction vessel was then sealed and stirred at RT. After 2 days, the reaction rnixture was vented with nitrogen and then concentrated in vacuo. The residue was chromatographed (PTLC, SiO2, 10% methanol/methylene chloride) to give N-hydroxy-1-[4-(4-chlorobenzoyl)-piperidine-1-sulfonyl]piperidine-2-(R)-carboxamide as a white solid (51%), mp 84.4-86.4° C.

Workup

  1. customHCl gas was bubbled through it for 10 min
  2. customThe reaction vessel was then sealed
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed (PTLC, SiO2, 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-beb559d31a0f4784a848cf6abe0a7017
Source dataset
uspto-grants-2000_10
Patent number
US06130220

Linked notes

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