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

HRID 609678

反応式

HRID 609678 の反応式
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]

参加物

8

反応物 5

HCID 312ChlorideHCID 79724-MethylmorpholineHCID 736316Pipecolic acid, (+)-HCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 187272151-[4-(4-chlorobenzoyl)piperidine-1-sulfonyl]piperidine-2-(R)-carboxylic acid

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-d6cf579b19bd4bec98e09124254890b6
出典データセット
uspto-grants-1999_12
特許番号
US05998412

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