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

HRID 609678

Reaction equation

HRID 609678 reaction equation
Cl.[C:2]([O:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].CN1CCOCC1.[Cl:15][C:16]1[CH:41]=[CH:40][C:19]([C:20]([CH:22]2[CH2:27][CH2:26][N:25]([S:28]([N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][C@@H:32]3[C:37](O)=[O:38])(=[O:30])=[O:29])[CH2:24][CH2:23]2)=[O:21])=[CH:18][CH:17]=1.C1C[C@H](C(O)=O)NCC1.[Cl-]>C(Cl)Cl.C(OCC)(=O)C>[C:2]([O:6][NH:7][C:37]([C@H:32]1[CH2:33][CH2:34][CH2:35][CH2:36][N:31]1[S:28]([N:25]1[CH2:24][CH2:23][CH:22]([C:20](=[O:21])[C:19]2[CH:18]=[CH:17][C:16]([Cl:15])=[CH:41][CH:40]=2)[CH2:27][CH2:26]1)(=[O:30])=[O:29])=[O:38])([CH3:5])([CH3:4])[CH3:3]

Participants

8

Reactant 5

HCID 312ChlorideHCID 79724-MethylmorpholineHCID 736316Pipecolic acid, (+)-HCID 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-ethylcaibodiimide 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-(4chlorophenoxy)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-d6cf579b19bd4bec98e09124254890b6
Source dataset
uspto-grants-1999_12
Patent number
US05998412

Linked notes

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