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

HRID 609678

반응식

HRID 609678 반응식
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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-d6cf579b19bd4bec98e09124254890b6
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998412

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