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

HRID 1856868

Reaction equation

HRID 1856868 reaction equation
Cl.[C:2]([O:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.[Cl:27][C:28]1[CH:53]=[CH:52][C:31]([C:32]([CH:34]2[CH2:39][CH2:38][N:37]([S:40]([N:43]3[CH2:48][CH2:47][CH2:46][CH2:45][C@@H:44]3[C:49](O)=[O:50])(=[O:42])=[O:41])[CH2:36][CH2:35]2)=[O:33])=[CH:30][CH:29]=1.C1C[C@H](C(O)=O)NCC1.[Cl-]>C(Cl)Cl.C(OCC)(=O)C>[C:2]([O:6][NH:7][C:49]([C@H:44]1[CH2:45][CH2:46][CH2:47][CH2:48][N:43]1[S:40]([N:37]1[CH2:36][CH2:35][CH:34]([C:32](=[O:33])[C:31]2[CH:30]=[CH:29][C:28]([Cl:27])=[CH:53][CH:52]=2)[CH2:39][CH2:38]1)(=[O:42])=[O:41])=[O:50])([CH3:5])([CH3:4])[CH3:3]

Participants

9

Reactant 6

HCID 312ChlorideHCID 79724-MethylmorpholineHCID 736316Pipecolic acid, (+)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 187272151-[4-(4-chlorobenzoyl)piperidine-1-sulfonyl]piperidine-2-(R)-carboxylic acid

Product 1

HCID 18727273N-tert-butoxy-1-[4-(4-chlorobenzoyl)piperidine-1-sulfonyl]piperidine-2-(R)-carboxamideYield 65%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

O-tert-butylhydroxylamine hydrochloride (127 mg, 1.01 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (129 mg, 0.67 mmol), N,N-dimethylaminopyridine (41 mg, 0.34 mmol), and N-methylmorpholine (0.15 ml, 1.3 mmol) were added to a solution of 1-[4-(4-chlorobenzoyl)piperidine-1-sulfonyl]piperidine-2-(R)-carboxylic acid (140 mg, 0.34 mmol), [prepared by proceeding as described in Example 9, but replacing D-valine and 4-(4-chlorophenoxy)piperidinesulfamoyl chloride with D-pipecolinic acid and 4-(4-chlorobenzoylpiperidinesulfamoyl chloride, respectively], in methylene chloride (2 ml). After stirring overnight, the reaction mixture was diluted with ethyl acetate, washed with 1M HCl, and brine, and dried over MgSO4. The organics were evaporated in vacuo and the residue was chromatographed (PTLC, SiO2, 40% ethyl acetate/hexane) to give N-tert-butoxy-1-[4-(4-chlorobenzoyl)piperidine-1-sulfonyl]piperidine-2-(R)-carboxamide as a white solid (65%).

Workup

  1. custom[prepared
  2. washwashed with 1M HCl, and brine
  3. dry with materialdried over MgSO4
  4. customThe organics were evaporated in vacuo
  5. customthe residue was chromatographed (PTLC, SiO2, 40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2724893c6b1d4baf9cda6f1f55a17476
Source dataset
uspto-grants-2000_11
Patent number
US06143744

Linked notes

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